(upbeat music) - Hello, and welcome to another episode of All The Hacks, a show about upgrading your life, money, and travel. I'm your host, Chris Hutchins, and each week I usually sit down with the world's best experts to learn the strategies, tactics, and frameworks that shape their success. Now, I've done a few solo episodes, but they've usually just been listener questions.

So today I wanna try something new and do a solo deep dive on a topic I've researched a lot. Now, I love to travel, and there are some amazing hotels around the world, but sometimes you just wanna stay at a vacation home, whether it's 'cause you want a kitchen, multiple bedrooms, or you just want a private pool or a balcony with an amazing view.

So let's talk about all the ways to make that happen. And when I say all the ways, we're gonna run through home rentals, fractional ownership, timeshares, vacation clubs, home exchanges, private residence clubs, and even vacation real estate investment funds. More on that one later. I spent a ton of time on this episode and have a bunch of topics I could do this on next, like insurance, parenting, credit card benefits, and a lot more.

So if you like this format, please shoot me a quick DM or email chris@allthehacks.com and let me know. Okay, let's get into it. But before we get started. All right, let's talk vacation homes. First, thanks to David, Scott, and Jesse, who all emailed me to ask questions or share tips on timeshares or vacation homes and ultimately inspired this episode.

So I'm gonna walk through all the options and what I personally think of each. And when we get to timeshares, I'll even share a few stories from my family's experience with them. So I'll start with the few options that have little or no upfront cost. The first, home rentals.

It's just what it sounds like. We've probably all done this. Renting a house, could be a condo or a villa on a platform like Airbnb, VRBO, or even directly from an owner. So I won't spend much time here, but there are a few things that I found when I was doing a little bit of extra research that I wanna share.

First, there are a few sites that seem to organize and curate just higher end properties, or at least properties with a more consistent design aesthetic or quality or set of amenities. One of them is Avant Stay. I've never used it, but it definitely looked interesting. And on the much higher end, there's one that I'm just really, really interested in called Wander.

They only have 11 homes, but they're all beautiful. Fast Wi-Fi, they have eight sleeps on all the beds, Peloton bikes, they even have a Tesla you can drive, and they have multiple high-end workstations with monitors, good chairs, microphones, everything you need. It's really the most turnkey rental I've ever seen.

I haven't been able to try it out yet, but if you do end up wanting to book something, make sure to email hello@wander.com and tell them I sent you, and they said they'd give you $250 off your booking. That is a referral link, but if enough people use it, I'll use the credit to go stay at a Wander and I'll let you know how it is.

A couple other sites. When it comes to really high-end homes and villas and resort properties, there's two sites, Haven and Villas of Distinction, which I think are probably two of the best sites with the most comprehensive set of properties around the world. But I will say there are a lot of local sites and companies if you're looking to go to different destinations.

So you really have to dig in. For example, in all the group trips I've planned to Cabo, I always use this one site called Cabo Villas. So this is not meant to be entirely comprehensive, but I wanna cover this category first because there's no upfront cost. A lot of the different ways that you could buy a vacation home or a timeshare or anything like that, you've gotta spend thousands, tens of thousands, hundreds of thousands of dollars upfront.

And this is one where if you wanna go stay somewhere, you could just book it. Now, the reason why all of these other options exist is because if you commit to various lengths of term or specific places, you can get a better deal. But if you're just looking for one trip, it's much easier to just book the place you want than worry about everything else.

So this is great for one-off trips. I will say the quality varies. I'm sure you've all stayed at an Airbnb that was great, and then you probably stayed at some that weren't so great. The price varies, the fees vary. I did see a post on Twitter that Brian Chesky, the CEO of Airbnb is finally gonna try to figure out how to kind of curb the craziness that is Airbnb fees, where it's here's the cleaning fee, the housekeeping fee, the booking fee and everything.

But I will say one thing that is tough is if you find a place you like and you wanna go there regularly, it's really hard to guarantee anything. Also, there are a lot of places that have restrictions on short-term rentals. And so there are some places, Napa being one of them, that it's really hard to find a home that you can rent because of all the restrictions on short-term rentals.

I will remind everyone of one of my favorite hacks for booking these places is take the photo of the property and save it to your computer and use a Google reverse image search and search for it. And you'll find that that property might be listed on five or six different sites.

And it might actually be cheaper on other sites. So I'd say use that trick. You might find that the place on Airbnb is 20% less if you book it on a local site, maybe like Cabo Villas or wherever you're looking for in the world. Next is home exchange. And this can literally be the cheapest possible way to stay at vacation homes around the world.

If you're unfamiliar and you've seen the holiday, you remember Kate Winslet, Cameron Diaz, swap homes across the world, fall in love. Well, I guess after that, I'd always assumed that home swapping was about finding a specific person or a family somewhere in the world that happened to have a home you want in the place you wanna go at the exact time you wanna go.

And they too wanted to go wherever you live. Well, the more I dug into this, the more I found out that the platforms that service home exchange have really evolved. And I was definitely wrong. There's actually a few different types of stays. Simultaneous being the one I just described where you find someone who wants to stay at your home while you stay at their home.

There's also non-simultaneous, which is someone wants to stay at your home maybe while you're traveling, and then you can find a time to stay at their home some future date. So it doesn't have to be lined up perfectly. There's also something called non-reciprocal. And this is where I think it gets really interesting, which is that most of the platforms have created some currency.

In one platform, they're called globes. Others, they're called keys. One of them, they're some kind of points. And by listing your home, you're able to have people stay at your home and earn this currency in the exchange program that you can then use on a totally separate house that the owners were never planning on even coming to where you live or staying in your home.

There's also something called a hospitality exchange, which is where you stay with someone and then they come stay with you, but you're not actually getting the house to yourself. But I'm gonna put that outside of the scope of this episode. So the most interesting one here to me is non-reciprocal.

I'll just share a few of the platforms here in case this is interesting, because I think prior to doing some of this research, this is something I never considered. And now all of a sudden, I'm a little bit more interested. There's Home Exchange. They've got 450,000 homes in over 100 countries.

Love Home Swap and People Like Us. Both also have thousands of homes in over 100 countries. If you already have a second home, and in many cases, even a fractional second home, which we'll talk about later, there's a site called Third Home, which basically lets you swap your second home for someone else's second home anywhere around the world.

Focuses on really high-end properties. The minimum is that they have to cost $500,000 and it goes all the way up to 50 million. On the total other end of the spectrum is Couchsurfing. There's 14 million members in 200,000 cities. This is something that I think early in life, I found to be incredibly valuable.

Amy and I did Couchsurfing all over the world when we went on our trip. And before we left, we hosted dozens of people in our home. This is definitely more like that hospitality exchange, except there's no real exchange. It's just a free thing that people do to get to know interesting people.

When we were doing it, we'd always try to leave some nice gift, but at the end of the day, there's no expectation of compensation. It's just a platform for travelers that like to meet other travelers and host them in their homes. I highly recommend it if you're going on a trip and you're willing to sleep on a couch or a sofa bed, or in some cases the floor.

And if you are, it's an incredible way to meet people and get to know a city. And I have so many great memories of Couchsurfing. There's one other cool site that a friend of mine actually shared with me called MyPlace. It's kind of like a hybrid of Couchsurfing, Home Exchange, Airbnb, where there's no real compensation.

It's not supposed to be a rental, but it's only open to friends and friends of friends. So they don't have the insurance policies that you would normally have. And you can ask people to either cover your costs or maybe pay for cleaning, but it's not a rental service. It's kind of interesting if you think, gosh, I'd be willing to let MyPlace go to friends and friends of friends, but I don't really want just random people to stay in it.

It's an option, or similarly, if you're looking for a place to stay, it might be a place to find a good deal if you have friends that live all around the world. If I can find discounts or referral codes for any of these, I'll put them in the show notes or at allthehacks.com/86, which is this episode number.

As for what I think, the overall benefit here is the cost savings, right? When you're traveling, your home is empty, so why not get something for that? Or even if it's not a straight swap, maybe you're visiting family for the holidays. Maybe you have a vacation planned already and your home's empty.

Why not list it on one of these platforms and earn whatever their virtual currency is and see if on your next vacation, you can use that currency to go somewhere for free. So some other cool, fun things I was reading as I looked in these exchange platforms, people include all kinds of things because it's really about getting to know the person even more than you normally would on an Airbnb.

So some people leave out their transit passes. Some people will let you use their car. Some people ask that, "Oh, you can stay here, "but you have to watch our dogs." So it's a little bit more of a person-to-person experience than just kind of a transactional book a property like you would with a rental.

But it seems, at least to me, kind of interesting if you can get past the obvious objection, which is having people in your house. In the past, we've had our place on Airbnb. And as we were thinking about what we could do now, we thought there were probably a couple rooms and closets that we could just add a lock on, get a little bit of privacy for some of our belongings.

Some of these platforms also collect deposits. Some have insurance. Some suggest maybe you should check with your homeowner's policy. But when I was looking online, even though these home exchanges aren't short-term rentals, the short-term rental coverages you can buy for your home often will still cover you. So I do think that if you can get over the fact that someone's in your house, staying in your room and sleeping in your bed, you can always buy a second pair of sheets, don't worry.

This could be a really, really interesting thing. Also, I'm not an accountant, so don't take this as tax advice, but because there's no money changing hands, I wouldn't expect you to get 1099s for your people staying in your home. And so it could be a little bit better even just from a tax advantage standpoint of renting your place and then booking places.

I might try it out, see what happens. If I do, I'll let you guys know. So those are two options that don't really require any significant upfront investment, but from all my research and personal experience, some of the programs that require an upfront investment can save you a ton in the long run if it's the right fit for what you're looking for.

Others can be a downright terrible investment, so let's dive in. And if the thing you really came for is timeshares, I just wanna make sure you know I will get to it, but I'm gonna get to a few things first. The most expensive option is to just buy an entire second home.

This one doesn't make sense to me because you can't be in two places at once. So unless you plan on renting them each out and effectively becoming a landlord because you can't be in the same place twice, which means you're gonna be renting out 365 nights a year, that's just not something I'm interested in.

So for me, this was never an option, and it's also probably the most expensive option unless you wanna turn it into a rental. So I'm gonna skip over that, but I think you all know how that works. You buy another second home. Fortunately, there are quite a few ways that you can buy into vacation homes for way less than buying an entire second home.

Some are effectively just clubs that you allow you to rent places, but others are true equity programs where you can have real ownership in the real estate and benefit from any of the appreciation. Unfortunately, there are so many different names when it comes to all of these things. There's timeshares, vacation clubs, fractional ownership and private residence clubs, destination clubs, luxury travel subscriptions, vacation real estate investment funds.

So to break this down, I'm gonna split everything into two categories. One, equity, where in one form or another, you're benefiting from the appreciation of the property, and non-equity, where members or owners don't have any ownership interest in the properties and don't benefit from its appreciation. I'll start with equity, and if you came here for timeshares, unfortunately, it's not in this category, and I'll explain more why later.

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So whatever the occasion, download the Drizzly app or go to drizzly.com. That's D-R-I-Z-L-Y.com today. Must be 21 plus, not available in all locations. But first I'll talk about fractional ownership. So this is true deeded fractional ownership in real estate. Could be as simple as buying a home with a few friends and doing the DIY version, all the way up to buying multiple homes with people you've never met before.

My favorite example in this category is Picasso, which full disclosure was how we bought our second home. And only after that happened did they become a partner of the show. And that's because I reached out to them because I really love the product and it's too bad they didn't reach out first.

Maybe I would have gotten a better deal on our place, but I think they explained the model really well. So Picasso will buy a home, they'll furnish it, put it into an LLC with eight member interests and sell those to buyers. So because you hold an equity interest in this home, you can get a loan from the purchase.

And when you wanna sell, you benefit from any appreciation. In fact, Picasso resales have sold in an average of 12 days with a 12% annualized gain. And I know that because I could see that I paid more than they did just a year before. So the benefit of doing fractionals through a company versus doing it by yourself is that they manage all the aspects of the property.

Cleaning, paying utilities and property taxes, landscaping, maintenance, repairs, and they usually have a system for scheduling and try to keep everything equitable between owners. I can only imagine that if you were trying to do this yourself and having to come up with a system about who gets to stay when, it could get complicated.

But not all fractionals are for just one property. I came across this site called My Five Homes that pairs you up with 20 other families who all collectively buy five homes. So as an example, one I looked at is planning on buying a home in New England, Turks and Caicos, New York City, Park City, and Maui.

So this isn't just about buying one property, there's all kinds of options here. If you couldn't tell, I love the fractional model because what we wanted was to have a consistent place we could go with a bit higher end furnishings than some of the Airbnbs we'd seen where we knew how everything was set up and more importantly, we could leave some things in onsite storage.

So for example, we have a bunch of non-perishable food, some clothes, a computer monitor, a dog bed, and more. So we don't have to lug all that stuff with us anyways. And the house itself actually also already comes with a crib, a baby monitor, a high chair, and all those things.

So for us, it was been so great. Also, there are a ton of restrictions on short-term rentals. So it's actually really hard and quite expensive to find a place you can rent with a few bedrooms for a family, but fractionals are true ownership and so they don't actually have those issues.

Now within fractionals, there's another category called private residence clubs. They're often described as high-end fractionals, but I've seen some really incredible fractionals that don't call themselves private residence clubs. So I'm gonna focus on the other distinction, which is that they're usually operated by luxury hospitality chains like Four Seasons or Ritz-Carlton and have the amenities typically found in high-end hotels or resorts.

These clubs often sell condos or villas with access to the club's golf course or ski resort, along with maid-cleaned rooms and turndown service. But a big selling point for some people is that owners also gain access to other properties in the chain's portfolio. So for example, up in Napa, there's a resort called The Orchard at Carneros, where you can buy a fraction of a two-bedroom condo, but the property is part of Timbers Resorts, so you can also trade your place in for a stay at their other properties in places like Mexico, Hawaii, or Colorado.

That said, I have a friend that actually has a fractional in Timbers, and he said you really have to be ready to pull the trigger the second you find availability at any of the partner resorts, because it's extremely limited and it goes really fast. Though another perk of private residence clubs is that some have a program that let you rent your place out if you're not gonna use it and either make some money or offset any of your annual dues that you pay for management or maintenance.

I assume some fractionals also allow this, but because private residence clubs are often at resorts, it's a much more turnkey experience. We actually considered The Orchard at Carneros because it was also in Napa, but for us, we didn't really want a two-bedroom condo that would change every time. We wanted a place that we could have all to ourselves that was big enough that we can invite family to come stay with us as well.

So if you're wondering what fractionals, including private residence clubs, cost, I'd say at the very entry level where you might only get a couple weeks in a smaller condo, you're looking at $50,000 to $75,000, but many are in the low to mid-six figures, and I've seen some fractions that cross into seven figures.

Like I said, another big benefit is that you can get a mortgage or a loan for fractionals because they're actual real estate, but you also wanna make sure that you budget for your annual dues to cover maintenance, management, property taxes, utilities, which probably is anywhere from $5,000 to $25,000 a year, depending on the property.

Next, I wanna talk about vacation real estate investment funds. When I first came across this, it was super interesting because in this model, a company creates an investment fund that raises money to acquire properties and then lets the investors in the fund use those properties at some rate proportional to their investment.

So it's almost like investing in a private real estate deal, except you actually get to stay in the properties. Now, a lot of private real estate deals are actually doing rentals, so there's less income, so I think the return on the investment might be more about the appreciation than the income, but it's still pretty interesting.

So the first example I found of this was called Equity Residences, which for their next fund is gonna raise $50 million to acquire 16 properties, mostly in North America and places like Hawaii, California, Florida, the Caribbean, and Mexico. And you can invest various amounts, but at the lower end, you can invest $200,000 and get one to three weeks of usage with annual dues in the few thousands of dollars.

So some cool things they do are they actually rent out properties when they're not in use to fund all the ongoing costs of the properties. And then they also list those homes on Third Home, which is one of the exchange sites I mentioned earlier. So you can actually exchange your time for properties outside of their portfolio.

But one of the major differences with this is around liquidity. The Equity Residence funds are set up to be 10-year investments. So while you can get your share of the appreciation of the portfolio when they sell, you can't just list your property or your share on an MLS site like you could with a fractional and sell it whenever you want.

You also can't get a mortgage because it's actually an investment as opposed to a real estate purchase. So if you're comparing a fractional share that costs 250,000 and a $250,000 investment on one of these funds, you might only need to put 75,000 down on the fractional while you'd need the full 250,000 for the investment fund.

That was a huge factor for us when we were looking at options, but maybe more importantly, was that we wanted to make sure that if we were gonna purchase a vacation home, we really knew we would get the maximum usage out of it. Otherwise, we knew it just wasn't gonna be a good deal.

And that meant we were looking for a place that was within driving distance of the Bay Area that we could go to regularly, and we just didn't find any of that with these fund options or private residence clubs. So those are all the equity options where you have real ownership in a property and benefit from its appreciation.

That's not to say the other options aren't a good deal. I just needed a way to split things up. And if you want links to any of the companies I'm talking about, I'll put them all in the show notes and on allthehacks.com. Now I'm gonna move on to non-equity and talk about destination clubs.

Now, depending on where you look online, destination clubs might be two different things. Some sites happen to say that destination clubs are actually equity, some aren't. But because there's no consistent definition, I've decided that I'm going to use destination clubs to mean non-equity programs where members pay an upfront fee to gain access to a portfolio of residences, typically multi-bedroom luxury homes all around the world.

And they typically come with the kinds of high-end concierge and hospitality services you'd expect at a five-star hotel. They're usually set up with a lower fee, like Inspirato starts at $600 a month, and then you just pay as you go for the properties. Or sometimes they have much higher fees that require no additional cost to use the properties.

So example, one of these is called Exclusive Resorts, and they charge $275,000 upfront and $36,000 a year in annual dues. But after that, you get 25 nights a year at their properties for the next 30 years. So there's a really great site I spent a lot of time on learning about everything I'm talking about called SherpaReport, and they have a comparison list of all the destination clubs, so I'll link to that in the show notes.

But I think the reason most of the people I've talked to seem to like these programs are two things, and neither of them really applied to me. One, they really appreciate the turnkey nature of the travel planning services, where you can say, "I'm going to this house in Italy," and someone will plan everything around that trip for you.

And two, the kinds of homes that they're looking to rent, you just can't rent on other sites. These two, five, $10 million homes that I've seen in a lot of these destination clubs just aren't on Airbnb that often. Also, from my math, it seems like you really need to be spending more than a few weeks traveling around the world, staying at multi-million dollar properties to get a good value, and that just isn't us, at least not yet.

Another thing, from Inspirato's investor presentation, since they were in the process of going public, I saw that their destination club project has a 67% margin, which means it's definitely a good business for them, but it made me a bit skeptical on the value I'd be able to get from it.

Now, I'm sure a lot of their customers aren't maximizing their memberships, and that's contributing to that margin number, and maybe if I signed up, I'd get a ton of value, but it was an interesting data point. Either way, I don't think it's the right fit for us, but speaking of Inspirato, they actually launched another product called the Inspirato Pass, which they're calling the world's first luxury travel subscription.

I saw a ton of advertising for it when it launched a few years ago, but I hadn't heard any firsthand reviews, so all of my thoughts here are based on research and blog posts. The way it works is a little complicated, but my best stab at explaining it is that you pay $2,500 a month, and every time you book a stay, it locks up your pass for a certain number of days.

So, if you wanna book the biggest, nicest property they have for two weeks, it might lock your pass up for eight months, but if you book a smaller place for a weekend, it might only get locked up for a month or two. Then, once it's unlocked, you can go and book something else.

I got a bunch of this understanding from this site Luxury Pass Review, where the author talks all about his experience with the pass and the tremendous value he believes he's gotten from it. In the 21 months he's had the pass, he said he spent $52,500, just 21 times 2,500, but he's calculated the value of all the stays he's had at $130,000.

So, it's definitely possible to get a good deal from the program, but in those 21 months, he's booked 70 nights, which is a lot of travel around the country, though, to be fair, 40 of the 70 nights he booked were at one specific property that I think was pretty close to him.

However, this made me think about the times where I've used my points to book a $10,000 business class flight. As much as I love feeling like I got so much value for my points, I'm not sure it's quite fair to call those points being worth $10,000 because there is zero chance that I would ever pay $10,000 for a flight if I didn't have the miles.

So, I wonder how much the guy that writes this site would have spent traveling if he was limited to only booking rentals or resorts, and whether he actually would have spent $130,000 or it would have been closer to the $50,000 he spent for the pass or even less. So, I can't say whether Destination Clubs or the Inspirato Pass is a good option or isn't for some, but I will say that you're gonna need to make a big commitment to travel and want it to be at very high-end properties and need those properties to have room for a lot of people since most of them are larger if you wanna make this worth it.

I wanna spend an extra minute talking about what I think is the best way to buy a vacation home. And as you know, we actually did it for our second home. I'm talking about Picasso and I'm excited to partner with them for this episode. So, how does it work?

Picasso buys amazing luxury homes in over 40 world-class destinations, creates an LLC for each home, and you can buy as little as 1/8 of the property. But it doesn't stop there. Picasso also professionally manages the home, handling design, cleaning, maintenance, bills, repairs, taxes, and more. When we found Picasso, it felt like it was made just for us, and within a few days, we found the perfect place in Napa, toured it, and the next week we were closing.

Since then, it's truly become our second home and has been so amazing. And it's true real estate ownership. Owners can sell at any time, set their own price, and tap into Picasso's active marketplace of buyers. In fact, on average, Picasso listings resell in 12 days with a 12% annualized gain.

For a modern way to buy and own a second home, go to allthehacks.com/picasso where our listeners will get a free Picasso access account, which means you can see new listings before they go live on the website and get up to $10,000 in credit towards closing costs. Again, that's allthehacks.com/picasso, P-A-C-A-S-O.

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Okay, time for the moment that at least a few of you who wrote in have been waiting for, timeshares. So with timeshares, you're purchasing the right to use a property unit for a specified time each year, or in some cases, a specific time or week each year, or in some cases, you're buying a timeshare, but it's really just a set number of points in a program, which it turns out is called a vacation club.

Either way, you don't really have any true equity ownership in the underlying real estate, which is probably why the resale values of timeshares is so terrible. But it can't be all bad, right? After all, almost 10 million households in the U.S. own a timeshare. My grandparents were one of them, and since they've passed, my parents became one too, so I've actually gotten a chance to see this from a few perspectives.

The good perspective was a few trips where our entire extended family went to Hawaii and Mexico and stayed at timeshare properties my grandparents had owned. In fact, my grandfather was probably one of the most frugal people I've ever met, so it's hard to imagine timeshares couldn't be a good deal, right?

Well, I've done a bunch of digging, and if you're okay planning your vacations very far in advance, and you've found a place you wanna keep coming back to for decades to come, and you're not looking for five-star luxury properties, I actually don't know if timeshares are the worst deal out there.

It's much less expensive than most of the options we've just talked about, with the average price of a timeshare being $21,455, and then a few thousand per year in maintenance fees. And I can tell you firsthand that I think my grandparents probably got their money's worth, because for almost 30 years, they meticulously used all five or six of their timeshares every single year.

But after they passed, and my mom had to figure out what to do with them, we saw the other side. Trying to get rid of them was such a challenge. None of their children wanted to inherit them, so after failing to sell them for anything, or even give them away, my mom actually had to pay the timeshare companies thousands of dollars to take them back.

So if you believe in market pricing theory, the fact that you can buy so many secondhand timeshares for a tiny fraction of their original purchase price would have to lead you to believe they're either not a good deal, or they're a good deal, but if you buy them secondhand, which is called a resale, it's an even better deal.

The deeper I went online, the advice was so consistent that if you're really interested in a timeshare, you're better to just go rent the places from owners that aren't using them, or buy one as a resale from another owner. And thanks to sites like Redweek, Tug2, and Go Koala, it's never been easier to do those things.

It's actually so crazy to browse those sites and see hundreds and hundreds of people trying to sell their timeshares for even just $1, or some of them will actually pay you to take the timeshare off their hands by prepaying a year or two of maintenance fees. But if all that's true, then why have so many millions of Americans bought them new?

Well, first off, the sales pitches are so good. I'm sure many of you have seen them while traveling or even been to some. They usually offer you a gift certificate, a spa treatment, or something to go to a presentation, but only if you're married and over 25. I know because I've been to a couple, and I just wanted to hear the pitch.

And if you're 100% confident you can walk away, then I'd encourage you to check out one of these and just see how it works. It's so crazy how good they make the deal sound. It's crazy to see the high pressure they put on you to sign on the spot, and the crazy incentives they'll roll out to get you to do that.

I loved watching it happen, but I happily left empty handed each time. I probably won't do it again on a whim, but I have gotten these letters from Hyatt and Marriott to go to some decent properties in Mexico and Hawaii. And it's like five nights for $400 as long as you go to the timeshare presentation.

Sometimes they even throw in bonus points. So I wouldn't be surprised if we end up taking them up on one of those offers in the future, but you can be assured that we are not going to end up with a timeshare. But I wanna loop back and cover a few of the nuances and answer a few questions.

First off, I mentioned you have to wanna come back to the same property, but I'm sure many of you that are familiar with timeshares are thinking, "Aren't there so many exchanges either through the timeshare companies or partners like RCI?" And I'll say, "Yes, there are." But they all usually give priority booking to the owners at specific properties.

So every time we've looked trying to use my parents' timeshare they inherited, it's been very, very difficult to get the dates we want in the unit size we want at a property that's worth staying at. But that makes sense because my parents are timeshare owners or technically vacation club owners and their ownership is tied to a really nice window in Park City.

And in order to book the three or four bedroom units they have that we use for our family vacations, you literally need to log into the website 13 months in advance at 1201 AM and book it before it's gone. Otherwise, you almost never get the dates you want unless you get lucky or you happen to be looking right as someone cancels.

Which brings up another interesting point on the downside of buying timeshares from an existing owner. So I know I said that's the advice I got but a lot of these programs especially at the vacation clubs where they're points-based have come up with tiers of status you earn as you buy more annual packages of points.

So you may have 500,000 points per year but if you buy another 500,000 and cross to the 1 million threshold you get an exclusive VIP status that lets you book yet another month before everyone else at certain properties. So to make their resales less enticing they only give you that status and those great advanced booking windows when you buy new directly from the property.

Funny enough, this is actually what happened to my parents. So they inherited a bunch of Wyndham points from my grandparents that based on the catalog of properties seemed like a great deal. Someone had to take them and we only had to cover the maintenance fees since my grandparents had already paid for them.

However, we quickly learned that it was just so hard to book the properties you wanted because they were getting snapped up so early. So despite years of family stories about how crazy it was that my grandparents were buying all these timeshares my parents went to one of these pitches to get their free gift certificate and left having spent thousands of dollars to get enough points that they crossed that magical million point per year mark and got that extra month to book things before everyone else could.

And to be fair they've used that to book a four bedroom unit at a place in Park City that's been a fantastic family vacation for us most of the past decade. And if you look at what it would cost to rent a four bedroom property in Park City I think the fact that they didn't have to pay for the original amount of timeshare points might've been a good deal.

But even given all of that they still keep rolling over hundreds of thousands of points each year because they're not using them all. And I finally talked to my mom yesterday and she said, if she could go back in time she'd probably have preferred to never taken over the timeshare and certainly wouldn't have bought all those additional points a few years ago.

So I guess my takeaway on timeshares is that you should definitely do a ton of research on the program you're looking at before you buy anything. That means joining the Timeshare user group forums or finding the owners Facebook groups and really trying to make sure you're gonna be able to get the value you want out of this because I can assure you anyone at a resort trying to sell you one of these is gonna make it clear that that value is so easy to get.

And specifically, I'd try to figure out if there's really anything you'd miss by buying a resale because you can get these resale timeshares for pennies on the dollar. And I do think there's some real value to be had on these resales. But again, you have to wanna stay at the properties within the timeshare program, many of which but certainly not all are pretty dated.

Also, if you're considering a timeshare, I would 100% make sure you try out the property first and sites like Go Koala make it so easy to rent other people's timeshares which might make you realize that you can just keep doing that every year and getting a great deal. However, I would love to hear from anyone listening right now that has stories or anecdotes around this topic so I can share back what I learned with all of you.

I can only do so much reading online but it would be great to hear all of your thoughts and experiences as well. So, that almost wraps up this vacation home episode but I did wanna share two more quick things that fit in line with the topic. Now, there are a lot of reasons to have a vacation home, timeshare, et cetera, but for some people it's because they just wanna go to a nice place maybe with a nice pool or resort amenities.

And if that's the case, there's actually two interesting companies you should consider checking out. The first is Resort Pass which lets you pay to use all the facilities of a resort hotel without actually needing to stay there. So, it could be that you're traveling and are saving money by staying at an Airbnb or maybe you even rented one of these timeshare weeks from Gokwala but you just wanna have a nice day at a beautiful pool or float down the lazy river or maybe you don't even wanna take a vacation or maybe you don't even wanna travel that far and you just wanna book a day at a resort close to home.

I haven't used it before but it's definitely an interesting model and there are a bunch of properties all over the country where you can pay anywhere from $20, $30 all the way to $200 to spend the day at. The second is Swimply which is kind of like Airbnb but for swimming pools.

So, when I searched near us, I found six pools within 10 miles that I could rent for 65 to $100 an hour. Based on the site, it seems like they're catering towards people who wanna host an event or a birthday party for their kids but compared to the cost of joining some type of gym or club with a pool, adding a pool to your property, staying at a resort or even using resort pass, for the occasional pool day, it's probably a much cheaper option and from their site, it looks like they're gonna expand beyond pools to tennis courts, home gyms, backyards and more.

As crazy as this might sound to some of you, I've definitely walked by some of our neighbor's houses who've turned their garage into a fully decked out gym and thought if there were some deal we could work out so I could use their gym, which probably sits unused 23 hours a day, I would totally do it.

So, if you wanna check it out, I created a Swimply account and you can use my referral code to get $25 off at allthehacks.com/swim and if any of you actually use this or resort pass, please let me know what you think and if I get enough referrals, I'll use my credit to book a pool and let you guys know what that experience was like.

Wow, so I had 14 pages of notes to do this episode and I think I've hit on everything on vacation homes. I was actually a bit nervous doing all this research because I went much deeper than I did when we bought our fraction of a vacation home through Picasso and I was a little worried that I would find an alternative and wish that I've done something different.

However, the opposite happened and I am now actually much more confident we made the right choice and because we're now gone five to six weeks a year at our Picasso in Napa, I'm actually thinking maybe we should start listing our primary house on one of the exchange sites and start building up some credits to let us stay in amazing homes on our trips abroad for free.

So thank you so much for listening. I'm curious to hear what you thought about this episode, both the content and the idea of doing these solo deep dives more frequently. Like I said at the beginning, I'm thinking of doing one on insurance, credit card benefits and parenting. Ideally the parenting one, I'll have Amy join me but if there are any other topics you want me to dig into or maybe there's just things about how I manage my own life you wanna hear more about, please let me know.

I'm Chris at allthehacks.com. Thank you so much. I'll see you next week. (upbeat music) (upbeat music) (upbeat music) (futuristic music) you