2nd home/cabin etc. How'd you decide to pull the trigger?

We bought a ski cabin in 2013 just as the second home market was beginning to recover. We had stayed in various VRBOs for 5 years before purchasing. In 2009 and 2010, it was impossible to get financing for a second home. You can definitely time the second home market and I would say now is the time to sell, not buy. Our realtor are estimating the current sale price on our cabin is about 300% of our purchase price. The second home market is much more volatile than the primary home market. I would say be patient and prepare for the right opportunity. Good luck!
 
Our primary home is in Michigan, but after I retired we decided we wanted to get out of the snow and ice during the winter months. So we rented along the Texas coast for several winters..........enjoyed that, but eventually decided to try the Florida Gulf Coast. Rented there for one winter, and really loved the location and the people. Great spot for kayaking, fishing, and the people were super-welcoming and friendly. We intended to keep renting the same house for the next few winters, but a neighbor came over one day and told us we HAD to look at a house that was going to go up for sale very soon, next to his house (this was 3 years ago now). The 92-year old guy who had lived there passed away recently, and his son did not want the house. His preference was to sell it quickly if possible. I really had no plans to buy a house down there, but we looked at the house (it was structurally sounds but needed some updating and repairs here and there), and asked him what he wanted for it. He said if we were able to pay cash, he would give it to us for XXX, which seemed like a fair price for the place. I still was not sure I wanted to buy a house down there, but my wife (and the neighbor) talked me into it. We had the place inspected (it passed), and talked to a contractor about how much $$ the priority work would cost (it was reasonable), so we took the plunge and bought the place. It's not like me to make quick decisions like that, but it has turned out well for us, and we have no regrets. We spend our winters down there now, and we love it. It's just a small house, but it's perfect for the two of us. When we are back in Michigan, we rent it out on VRBO/AirBNB (we have a great local property manager - I would not rent it without having that). The rental money we take in pays the taxes, utilities, and more, so that's been nice.

My advice: life is short. If you think you would really enjoy a vacation home, and you can swing it financially, do it. Renting is okay, but when you own a place, you can really make it your own, and there is satisfaction and pride in that. We get comments all the time from people that rent our house saying how much they love the place, and the location, and that makes us feel good. I don't know how long we will own this place........hopefully for quite a while, but we have already gotten a lot of enjoyment out of it.
 
DW and I have been having discussions about buying a beach house or a cabin even though our first mortgage isn't completely paid off (but close). If you have a 2nd home/cabin/beach house, how'd you pull the trigger and decide to buy one? Or did you inherit it? As someone on the FIRE path, it's really hard for us to do that vs say just doing like a VRBO for a month.

We bought ours in 2010 at age 50 knowing it would be our forever home in 5 more years.

What made me make up my mind was when my cousin died. Same age as me. Made me pull the trigger.
 
I totally understand the appeal, but I don't want the responsibility of another house for now.

But, never say never . . .
 
We were able to pay cash for a modest place in So FL in 2011 when the price was still near the bottom. It would have been harder to take the leap in today’s market. I was also still w*rking then with nice income, so that made it easier.

It’s been a great decision. Value of the house is way up now and we’ve spent a ton of time there especially after FIRE. I certainly wouldn’t change anything and you can’t take it with you!
 
Tough decision

We’ve been waffling on if/when to build our next home while still living in current home. Properties are similar in current and projected costs. 3-4 year target. Comments on thread about life being short, do it now vs obvious extra expense of having two homes. We still can’t decide, which as the song goes means we still have made a choice 😂
 
I recently bought a vacation lake house. I’ve been considering a 2nd place for years. I wanted to live someplace with a nice view before I die. With my experience of the pandemic and deeply realizing life is short, I got to work and found a beautiful place with a view of a beautiful lake. The thing that tipped me over, my 83 yo Mom asked me what I was waiting for. [emoji41]
 
Yes, second homes are an expensive splurge. My sisters are keen to keep the family lakefront home when my mom dies... the annual property taxes and upkeep are about $13k a year, but the other thing to consider is that you have a $400k investment that earns nothing and the opportunity cost of money on $400k at 4% is $16k... so your total economic cost is about $29k.
Made me look. We have four children and set up our home so that we wouldn't feel the need for a lake house but at one point in our careers we had a period where we had summers off and rented a few places. We fell in love with the lake and our young children greatly enjoyed the experience so we pulled the trigger in 2006 on a place 3 hours away.

Doing the calculation, the annual return has been the equivalent of 6.6% after expenses and taxes. Not too bad and this could have been much higher if we had rented out the place for even a few weeks a year. Not S&P 500 but not too bad for something that was much more a family luxury than an investment.

Our children are now all in their 20s and although there was some waning of interest in their late teens they are all now very much back into going to the cottage.

In my mind, as mentioned, the main decision is whether you feel that the value of having your own special place has more upside than the potential downside of being committed to a place that would limit other travel opportunities.
 
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How did we pull the trigger?

We knew from day one that we wanted rural property. As life progressed when:
1. Watched a close relative get hit with early onset dementia
2. We realized we kept talking about vacations but not taking them.
3. Decided a closeby cabin would fix #2.
...we got more serious.

Thats how we decided, in principle, to get a vacation property.

How did we decide on the specific property. Simple. When we drove up to the dilapidated 1970 era ski cabin in foreclosure we just knew. It was like at first sight.
 
If I were ever in a position to have more than one home, I would want at least one of them be a townhome or condominium, so I didn't have to do outside maintenance on more than one property.

Perhaps a small townhome for my primary residence and then a country cabin which would be nice when I wanted a totally different atmosphere or my primary residence having a yard but the vacation home being a condo. Those wouldn't be totally free of maintenance concerns (as someone is still typically responsible for HVAC units, indoor plumbing, etc. in many townhomes) but it would seem to eliminate a lot of them.
 
We debated buying something down in Mexico since that seems to be our "go to" place to relax. The Air Force did a great job of letting me see the rest of the world, so I am fairly content on hanging around in MX when I want to leave the country.

However, my MIL/FIL own a second home that is in the mountains and about 1.5 hours from us. It's rarely used by *any* of the family but there are plenty of costs associated with it. They also own(ed) a boat house that was used A LOT over the years but the family stopped visiting often as they aged...partying on the lake isn't as appealing when you get older. It was sold for a nice amount of money, but it too wasn't cheap to keep and the slip rental wasn't cheap AT ALL.

So, we have decided to just rent when we travel. Since we aren't spending money on a second place, we tend to splurge on the places we stay (almost always single family homes).
 
If I were ever in a position to have more than one home, I would want at least one of them be a townhome or condominium, so I didn't have to do outside maintenance on more than one property.

Perhaps a small townhome for my primary residence and then a country cabin which would be nice when I wanted a totally different atmosphere or my primary residence having a yard but the vacation home being a condo. Those wouldn't be totally free of maintenance concerns (as someone is still typically responsible for HVAC units, indoor plumbing, etc. in many townhomes) but it would seem to eliminate a lot of them.

We've got that... our primary residence is our winter condo which is easy peasy.... and our summer residence is a SFH that is a lot more work. DW loves the SFH because she likes to garden or as I call it "play in the dirt".
 
We lean the other way. We specifically wanted a sfh so we could garden (flowers and vegetables) as well as sit in the backyard with the dogs, grill, have fires in the chimanea, etc. We already had a mango tree, although we're never there for harvest time. But our neighbors and lawn guys love them. But we've planted a Meyer's lemon tree, a lime tree, a honey bell orange, and most recently an avocado tree. More lemons and limes than we know what to do with. The orange tree is putting out a few fruit so far, and the avocado will probably produce next year. Heck, I've had a Jalapeño plant that lasted over 2.5 years and produced hundreds of peppers. Gotta love FL for plants.

I don't think we could do most of that on a lanai or patio. But I really do understand the draw of simplicity. Especially as we get older.
 
My ex and I owned a cabin the mountains for about 8 years. We bought it when I was in my late 30s, when my projections showed that I could still retire when I wanted if we slowed down our after-tax savings to buy it. It was about 2 hours away; we went most weekends in the spring/summer/fall, and occasionally in the winter.

I loved it, but it did stop us from doing other weekend trips - why should we pay for a hotel in X, when we have a cabin 2 hours away?

We got divorced, and I started using it less, and sold it. I don't regret it, but it was never going to be my "retirement" home.
 
About 5 years ago my wife and I decided to buy a second home/condo so we started looking near the nearest Gulf Coast beaches for something on an intercoastal waterway. We stayed in several different places to test them out but the traffic and influx of people, especially around summer holidays, was just too much to deal with and the maintenance costs and capital improvement assessments in a lot of places were unpredictable and/or outrageous so we changed direction and started looking on local rivers for a standalone property.

After almost buying a house on a local river before the owner decided to lease the place just as we were about to make an offer we found a river lot with a 1BR/1BA boathouse we both loved. It needed a new septic system ($$) and we added a new covered boat slip and bought a new center console to go in it ($$$$) but it is now our every weekend happy place.

It is only a 20 minute ride from our primary residence and is 30 minutes from beaches. In a couple years we're going to build our forever house on the river and sell the primary home but there's no rush. I originally took out a mortgage to purchase the river lot but ended up selling some bonds and using the proceeds to pay it off last year.
Life is good and especially good when your happy place has no mortgage.
 
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I waited until I could pay cash for 2nd home on favorite lake. It’s an opportunity cost, but helping not hindering my lifestyle.
 
We've got that... our primary residence is our winter condo which is easy peasy.... and our summer residence is a SFH that is a lot more work. DW loves the SFH because she likes to garden or as I call it "play in the dirt".

That sounds wonderful! :)

And your profile states you're in SW Florida and Vermont, so you picked well in being able to go from one climate to another at the most opportune time.
 
A different approach

We thought seriously about getting a second home on the ocean but realized the upkeep would be huge (check out the HVAC systems on oceanfront property to see how often they will have to be replaced, particularly in the Southern states that we wanted), and knew that hurricanes would cause havoc with the insurance marketplace. So we went all in on the timeshare angle, specifically Wyndham, and are loving it. We stay three months every winter in a nice oceanfront unit in the North Myrtle Beach area, and because we prefer to travel during the offseason we have tons of discounted points to use every year. We currently travel about five months out of the year and have thought about possibly going homeless and traveling fulltime, through a combination of timesharing, BnB, home rentals, and hotels. Have met a number of people that do just that so it is very possible.
 
why stress over it?

A lot of very sensible replies here, but also a lot of agonising over something pretty simple. If you have the money and it is something you want, why hesitate? We actually purchased our "second home" before we purchased our primary residence. It's just how it worked out at the time and we don't regret it at all. It's a 1.5 hour flight and 5-6 hours door to door (London to rural France).

We used it as a secondary for about 6 years, but it's been our primary since covid lockdowns started in Feb 2020. Once we can move freely again, we'll start looking for a new "second home".

Life.Is.Short.
 
We bought a vacation rental home in SW Florida in 2010 without much worry because prices were down and we rent it more than we use it. It pretty much pays it way and has now doubled in value. We then bought a cabin in 2017 in a condo complex at a popular lake 1 1/2 hours from our house. I had a tougher time justifying that purchase as we do not rent it so no money coming in or tax benefits. The kids/grandkids love it so we are glad we did it. We don't have a pool at home but both vacation properties do so that has been nice. I am getting to the point of my life where I wonder if I focused on saving too much and now have to loosen the purse strings.
 
A lot of very sensible replies here, but also a lot of agonising over something pretty simple.

Dude... If it wasn't for over analysis we'd have no analysis at all around here. ;)
 
We are on the other side of that question. When our kids were younger, we got our second home - a mountain cabin that had 4 seasons of activities. The whole family loved it and it was only 2.5 hours away.

However, after about 15 years we found ourselves going less and less and the maintenance costs getting higher and higher we pulled the trigger last year and sold it. Even though we paid cash for it and didn't have a mortgage, the monthly recurring costs were pretty steep. Plus I was getting annoyed at doing two homes' worth of maintenance.

Bottom line - it was great to have it and it was great to sell it. If it works within your budget, I say go for it. And if it doesn't work out, it could still be a grand adventure.
 
We are on the other side of that question. When our kids were younger, we got our second home - a mountain cabin that had 4 seasons of activities. The whole family loved it and it was only 2.5 hours away.

However, after about 15 years we found ourselves going less and less and the maintenance costs getting higher and higher we pulled the trigger last year and sold it. Even though we paid cash for it and didn't have a mortgage, the monthly recurring costs were pretty steep. Plus I was getting annoyed at doing two homes' worth of maintenance.

Bottom line - it was great to have it and it was great to sell it. If it works within your budget, I say go for it. And if it doesn't work out, it could still be a grand adventure.

Those are good things to keep in mind. Especially if the whole purpose for retiring is to reduce stress and there's the aggravation of keeping two properties up.

And while it's not something that applies to you since it looks like you owned the property outright, this thread and the ongoing maintenance costs made me think of something that I can't imagine would be a good idea and I've never heard of anyone buying one who is glad they did. That's a timeshare. Someone is basically pre-paying for a vacation and offering a blank check for various ripoff fees. But I think most people in this audience would realize that.
 
We did that

Those are good things to keep in mind. Especially if the whole purpose for retiring is to reduce stress and there's the aggravation of keeping two properties up.

And while it's not something that applies to you since it looks like you owned the property outright, this thread and the ongoing maintenance costs made me think of something that I can't imagine would be a good idea and I've never heard of anyone buying one who is glad they did. That's a timeshare. Someone is basically pre-paying for a vacation and offering a blank check for various ripoff fees. But I think most people in this audience would realize that.

Read my earlier comment above. We did exactly that and are extremely pleased. Our going heavily in that direction to travel ~5 months out of the year started about ten years ago, but we have owned a couple of weeks in another system for about 35 years now. No complaints and the costs have been reasonable to us, certainly compared to the maintenance required for oceanfront property that we would have wanted. And I don't have to maintain a second home; I already do all the work around our large home as it is.
 
We never wanted to deal with a second home, so we bought a traditional timeshare (2 weeks) in northern Vermont that we could drive to in under 6 hours (no flying hassles), staying in the same condo the same weeks every year, except for times we wanted to exchange to go somewhere else ( and we did travel all over the country with weeks we exchanged. Plus some years we added an additional non timeshare vacation to somewhere else ). In VT, we got to see the same folks every year at the pool and during some of the activities, and it always felt like we were “ home”. 22 years we owned and our family loved it. It was worth every penny that we paid for it as we used it every year. It paid for itself and then some (we originally paid cash for it) and the majority of owners there would say the same. There kids and grandkids are still coming up year after year. Many memories made.

Some people there own quarter years, half years or full years.

We liked it so much we bought a third week at another resort in NH just 2 hours away from the VT one and that fell exactly after the fixed summer VT week we owned. ( the other week always varied during the spring or Fall).

Now that we are retired and have moved to NH (in the heart of a big vacation area) and are older we decided to take advantage of a take back program the resort offers so we no longer have the two VT weeks. Bittersweet. Our 33 year old single son couldn’t afford to take it over or he would have in a heartbeat. He visited with us there every year right up until last year. He is very sentimental about it. It’s just that kind of place.

We still have the NH one as it’s just an hour away and we have day use of the facilities as an added benefit. It’s in the White Mountains and we live in the Lakes Region so we have the best of both worlds.

Anyway, for us it was a carefree way to have a second home without the big expense and upkeep.
 
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