re: Dream retirement housing split

What is your budget?

Mountain Options:
1. Jackson Hole - Simply the best
2. Telluride - Similar to Jhole, just less
3. Park City - pretty awesome being so close to a major US City (SLC is less than 40 min)

Beach Options (are you elite?):
1. South Hampton? Nantucket? Martha's Vineyard
2. Grayton, Seaside, Destin

Links like Fairhope and Santa Fe for me

Summer in Tuscany
Winter in St. John or the BVI

TBH I'd probably buy one beach house in NC or Charleston.

Then AirBnB to a bunch of mountainous locations each year. Way too many beautiful spots to commit myself to two

G

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Your plan has a fatal flaw. You are going to want to be using the houses in the locale when they are at their most desirable. Ain’t nobody wanting them in the off season.

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Depends on how creative you are. We live in Key West Florida. We don’t plan on renting out our primary house. We rent out a place in Vermont year round, but eventually we’d like to rent it out during the school year and live in it during the summer. If you rent to college students you can use it during the summer. Eventually we’ll stop renting it out at all (after it’s mostly paid for).

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My father in law has about a perfect combo:

Primary on large lake in central TN
Ski in/ out in Jackson hole
Beachfront condo in So Wal

Personally, I wouldn't get a 3rd property unless you have a history of being there a lot. I'd get one place to "winter" or summer, and then live by your friends and family. Try as you may, vacation homes you simply don't have a local network really.

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Three places are a lot. I have friends who have 3 and they haven’t been to the third place in like 4 years. Key West, Houston, Montana.
Even people that have two find themselves stretched a bit. Some friends of mine that split between KW and MD don’t come down as much now that they have grandkids in Seattle and MD.
You also take winter and summer vacations from where you live that time of year.
I think two is enough, but I couldn’t rent out both when I’m not there. One place has to be your “sacred” place where you keep all your private/personal stuff. A second home you can treat as a part time vacation home.

Pick places that have airports and are easy to get to so that family can visit easily or so that you get get in and out quickly if need be

I think a lot of people like the idea of splitting time and owning two places but it ends up being too much work in the end. Instead, they rent one / own one.

The wife wants to do 6 months denver / 6 months new orleans but she wants houses in both places. Sounds like a ginormous pain in the arse to me.

My preference is to buy a 2 bdrm condo in denver, and then travel all winter.