Houses are easy and cheap to change.

Location is king.

Just a thought, how about near Asheville NC? Not too far from world class medical centers, or Wendel's family, good temperate weather if you're high enough in the mountains. Famously progressive.

My son is considering moving there.

Played at a music festival there a year or so ago. Really liked the atmosphere.

The problem with places like Asheville is that you are a small island of progressive in a giant state of dumbass. Trust me - Philadelphia and Pittsburgh are the same way. While we can sometimes swing the presidential elections our way through sheer numbers and usually manage to elect a dem governor, the state is hamstrung by an ass-backwards republican legislature that gerrymanders creatively to make sure they stay in power. They block everything from gun control to abortion rights and the governor pretty much spends his whole term vetoing whatever stupid legislation they've come up with to pander to their base. And once you get outside the metro areas, the idiot factor (measured by my unoffical scale of Trump signs/flags/bumper stickers per capita) is high. Really high.

If I were looking to move elsewhere, I'd look only at places where the whole state is pretty progressive and where the vaccination rate is high - the vaccination/case count rate right now is a good yardstick for how stupid/conspiracy-theory-oriented the populace is in general. For me, that would probably limit me to Massachusetts or Vermont, maybe New York. I might look near college towns too - if there's a med school (like UVM) you'll have good medical care and the college campus will draw lots of cultural things even if you aren't near a big city. Honestly, I might consider Canada too, though I'm guessing they might not look at retirees as desirable immigrants as they are likely to be a drain on the healthcare system.

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The problem with places like Asheville is that you are a small island of progressive in a giant state of dumbass.

Can confirm....

What about Canada? Being in Montana, you’re right next door to it.

If you have Medicare for your primary health insurance, it’ll only cover you for a certain number of days per year if you were to live in Canada year round.

My parents wanted to retire in the Toronto, Ontario area. They liked the city. They decided not to move there after looking into the whole financial picture. There’d be no problem with moving there. But they said there would be some financial penalty if they wanted to move back to the U.S. I don’t remember what the penalty was or which country would impose it. I wouldn’t mind moving to Toronto myself. I rather liked the city.

You could board your horse on a horse farm instead of on your own property. My sister owns a horse and that’s what she does. The horse farm is about 10 miles from her house.

I like Asheville. I've visited there multiple times. It's perhaps a little small to offer all the amenities you might seek. I've sometimes said that if I were to move from the Pittsburgh area to someplace a little warmer in wintertime, the SW Virginia, E Tennessee, W North Carolina area is a region I'd look more closely at. I do love the higher reaches of the Blue Ridge mountains.

Here is another vision for a place to live: Kingston NY: What Happens When a Buffett Buys Your Town?

Big Al

That story about Kingston and Peter Buffett is fascinating and also very strange....

I do not want to live in the South, period. What is happening there politically--as Lisa described so accurately--is what has recently happened to Montana. There is also something about that culture--the phony genteel "well bless your heart" crap--that sets my teeth on edge. Gah!

Big Al you would be a delightful neighbor!! Maybe we need to create our own retirement community .

I am leaning towards the Berkshires. That's where I went to music camp in the 60s. And when I lived in NYC it was a favorite winter getaway. Plus another very close friend has just moved to that area. I just wish I knew why housing is so much cheaper there, if there's something I'm missing.

Same with western Virginia: why are there so many wonderful and affordable properties there, what are the drawbacks to that area? Wish PianoDad would weigh in on this.

I don't like humidity and bugs, but MT has gotten so dry, and plagued with grasshoppers, I might prefer to return to the East after all.

In the opposite direction--We just booked an airbnb for Whidbey Island in 2 weeks. Leading edge in progressive politics (high vaccination rate), kind hearted, creative neighbors, easy access to Seattle, water views and public forests and beaches. and even a horse community! We even have a RE agent we found through Zillow who is sending us properties to look at.
We're driving over and will also stop and look at Spokane on the way.

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western Virginia: why are there so many wonderful and affordable properties there, what are the drawbacks to that area?

Could it be because there aren’t good jobs? That’s an impression I have, no idea how accurate it is. But if so, it wouldn’t necessarily impact you…

I think it's because both locations are pretty rural. Not a whole lot going on, not close to big cities. I know Western Mass has Springfield, which is a mid-sized city with hospitals and U Mass/Amherst/Holyoke a bunch of other colleges are there, but once you are out of that area, it's pretty rural. Western VA I would think is the same way - you do have some colleges out that way (Va Tech, James Madison, but also be warned - Liberty University!) but other than that, it's just rural and there's not a lot around. Western VA strikes me as a bit more conservative/religious/probably not your sort of folk than western MA, but I haven't spent a ton of time in either area. I do think that once you are out of the NoVA I-95 corridor/DC area, though, VA becomes pretty Southern so if you don't want that, you may want to rethink.

However, this occurred to me: we drive through West Virginia a lot going back and forth to Ohio. Morgantown, home of WVU, is supposed to be really nice and the scenery is beautiful. And as I recall, WV did surprisingly well on the covid front - their governor was all in pretty early on with restrictions and vaccines and they came through with much better numbers than you'd expect. Also, they don't seem to be steeped in the southern culture you want to avoid. Might be a surprise contender!

I agree with Lisa regarding western Mass - not a whole lot going on, not a lot of jobs. Obviously that wouldn't be an issue for you. However the area is beautiful and the politics defnitely lean progressive. The winters shouldn't bother you, I assume, since you're used to Montana. Also, there is reasonable access to world class medicine.

Re: Whidbey - great place, beautiful and spendy. It's also not at all easy to get in or out during the tourist season, which runs from around May - October. There's only one way on and off the island (duh), the ferries are fully booked, and the traffic is horrible. I've waited to get past the Mukilteo exit on I-5 for up to 1.5 hours of stop and go traffic, in both directions. So "easy access to Seattle" is definitely not true for at least half the year. I drive up and down I-5 a lot, and it's always touch and go in terms of traffic from Tacoma up through Everett. Some days it's a breeze, other days it's stop and go.
Random option might be someplace like Walla Walla, where Whitman College is. It's become a real center for wineries, etc. The town itself is small and charming imo, and Whitman provides a dose of intellect and activities (concerts, theater, etc.). But you are in the middle of freaking nowhere.

Walla Walla is fun but crazy touristy, it’s been totally discovered, we had lunch there on the way to pick up Katie. And they have terrible temperature wood smoke inversions in the winter.

You are right about the ferries in western Washington. Very difficult to get one in convenient times in the summer (with a Car) the only way off without a ferry is out the top through Anacortes, cool town too, but it is not a bargain to live there. And the traffics down the I-5 corridor is AWFUL. Traffic isn’t particularly easy on the island either. It was bad when we lived i whatcom county, and that was awhile go. Lots of folks love the islands up there! Also need to think about sunshine days anyplace in western Washington. (That kind of thing effects me, part of the reason I like Montana, Billings was awesome for sunshine.

Seriously, any place that has the things we want others want too, and all this work remotely stuff has pretty much made those places harder to find houses in. My experience (based on many moves) is you look forward to getting away from certain problems where you live only to end up with a whole set of new ones where you go. Boarding horses over there is pretty pricy too…

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piqué
I am increasingly less tolerant of people who are unsophisticated and uneducated and with whom it is impossible to have a thoughtful conversation. It's not that they aren't very nice folks in most cases--they are. They'd give their right arm for you if you were in need--a great many of them would.

Maybe the wildfires will clear out the riffraff and cool off the housing market. One can hope.

I thought I'd pop in to see how y'all doing. Then I read this and remembered why I left. Entitled or entitled, eh? Shameful.