I don't have a lot of foreign countries on my list, though they're interesting. I might have to look more into them.

You'll have to find some more pirates & barges so you can see the world.

Panama was on my list too. I hear good things about Boquete. Maybe go back to Austria. I may find an obscure spot in the US to be a hermit.

If I just lived on freighters, I wonder what the tax situation would be. Would I be taxed according to the ship's flag? Or would I not be taxed at all? I'll have to talk to the wife about this possibility.

#51 through 55. Some interesting ones here. See the picture for the details and scores, as usual.

51 Overland Park (KS)
https://www.realtor.com/realestatean...-51725?view=qv

52 Davis (CA)
https://www.realtor.com/realestatean...-22479?view=qv

53 Fredericksburg (TX)
https://www.realtor.com/realestatean...-20710?view=qv

54 Placerville (CA)
https://www.realtor.com/realestatean...-96694?view=qv

55 Ketchikan (AK)
https://www.realtor.com/realestatean...-79162?view=qv

Summary (starting from the bottom)

Ketchikan, AK – I'm kind of in love with Ketchikan. It’s the most southern point in southeast Alaska, so it’s closer to Seattle than Anchorage. First, look at the view from the sample house. It’s incredible. Second, the sample house has an apartment with it, which I haven’t accounted for in the finances. Third, Ketchikan is a major cruise ship stop, so it’s got outsized retail and restaurants for a small town. Fourth, Alaska has a ludicrously good tax structure, so this is the most affordable place in my entire tournament. I could almost move there now and retire. Fifth, the ferry stops in Ketchikan, so we can comfortably travel to Vancouver or Juneau for a night on the town. This is actually a really intriguing place. It does get snow, but it’s 13 degrees warmer in winter than Denver and gets less than half the snow. The only downside is that it gets a ton of rain and clouds and the summers aren’t warm.

Placerille, CA – I know nothing about this place in north-central California, but was trying to find a place that’s a little higher and might be cooler than other central California places. This town seems nice. It’s no more cost effective than staying in Denver, but it’s 20 degrees warmer than Denver in winter and only gets traces of snow. The summers are about 5 degrees warmer and a little more humid, though, which I don't really like. It seems to have a nice housing selection.

Fredericksburg, TX – Nice house on two acres in the Texas hill country. Texas has a nice tax structure so it’s affordable. The winters are mild, but it’s still a Texas summer that’s hotter and more humid than Denver. It leans pretty far right politically and we might have to learn German. It’s interesting but risky in some areas. And I still remember those giant roaches from my time in Austin.

Davis, CA – College town in north-central California, so it’s very left-leaning. It’s a nice-sized community with a decent housing selection. The winters are nice and mild, though the summers are 5 degrees warmer than Denver and more humid. It’s nice in many areas, if not a standout in any area.

Overland Park, KS – Slightly more affordable than Denver with a lot less snow, but a midwestern summer. The condo sample is really nice and it’s in a nice-sized community, but I don't like midwestern summers.

By the way, I kicked Nebraska out of the tournament. I had a business thing in Omaha and everyone I encountered was a complete jerk. So screw Nebraska. They're out. I replaced them with another place that looked interesting.

Hmm, interesting that it would score higher than Vancouver, but I'm sure it's more affordable (and as you mentioned with taxes). And for it to be that much warmer than Denver. Granted, the 100 sunny days...

I've been on one cruise and actually felt bad for a couple of the small towns.... I could imagine how quaint and quiet they were, and now every once in a while 3000 people flood the streets. It does boost the economy though.

Yeah, affordability is the main difference. I'm not even accounting for that annual payment that Alaska makes to its residents, so it's even more financially friendly than shown.

I figure the cruise thing is probably something you can avoid once you know the schedule. You hole up when they're tramping through town, and then you come out of your burrow when they're gone and the restaurants need business.

My wife will have an issue with the clouds and rain, but I wouldn't. I'm a shade lover and I don't mind rain.

Vietnam would be the cheapest, however if you choose to retire there you won’t be able to receive social security.

Yeah, I lived near the Kansas Speedway, and granted it was only a few times per year, I just got used to avoiding that whole area on those weekends.... so, as long as you're not in the direct path of the hoards of tourists (or don't mind being so), they're probably easy enough to avoid.

Didn't know they had an annual dividend... an extra ~$1000/year, nice.

And that's per person. It was $1,600 per person the last couple of years, so this is a down year. That's a good deal for the average person.

My wife says Barbados is offering 12 month visa for people who will come there. If she can find us some remote jobs that can be done from there, we might just jump on it. Only owe 75k on this house and I could sell it for at least 200k. Would love to go live there for a year!

I made a brief visit to Barbados once. I was only in the touristy area, but it seemed pretty nice.

Holy cow. Not only did my wife not shut down Ketchikan, but she said it sounded really interesting. She suggested that at some point we spend a month or so there just to see what it feels like to live there. I'm staggered but delighted. I'm very interested in Ketchikan.

#46 through #50. See picture for scoring and stats.

46 Fallbrook (CA)
https://www.realtor.com/realestatean...-31376?view=qv

47 Roatan (Honduras)
https://www.realtor.com/internationa...-120051079293/

48 Hilton Head (SC)
https://www.realtor.com/realestatean...-09319?view=qv

49 Incline Village (NV)
https://www.realtor.com/realestatean...-66838?view=qv

50 Palm Springs (CA)
https://www.realtor.com/realestatean...-48729?view=qv

Summary (starting from the bottom)

50 – Palm Springs – It’s a great place if you want a mild winter, though summer descends with hellish force. (But hey, very low humidity.) There’s a very good selection of affordable houses. If you look at the layout of the sample house, it’s a perfect one-story layout for a couple who likes to go to bed at different times, and it comes with a pool and hot tub. Mmmm. It would rank higher except for the classic California tax problem that makes it less affordable than staying in place. I’d have to work 6 months longer to afford it compared to staying in Denver.

49 – Incline Village (NV). This is Lake Tahoe, but on the Nevada side where taxes are cheaper. Because it’s Nevada, it’s very affordable, cutting about 1.5 years from my retirement schedule. However, it’s a ski resort, so the winters are big on snow with more than double what we get in Denver. I don't ski, so that's not a benefit. The summers are kind of perfect, though, topping out under 80 degrees. The other problem here is that real estate is expensive, so we would have to get a home that’s half our current size. I’m not feeling this one despite the affordability.

48 – Hilton Head (SC). It’s actually quite affordable, cutting a year or so off our retirement schedule, and the winters are very nice. The summers are hotter than Denver and a lot more humid, though. I don’t think I want that. The housing selection is okay - neither inspiring nor offputting.

47 – Roatan (Honduras). This is a large resort island off the coast of Honduras that’s well known as an expat location. You can get a nice house here and never have cold weather. I’m guessing a bit on affordability since I didn’t look at taxes here and just assumed a Denver level. However, I took a quick glance, and it actually appears that taxes are higher here. So it should move down the rankings. It loses points mostly because it doesn’t have any cool weather, with a January low that averages 82 degrees. Kind of interesting, but probably just as a lark. I'm really not a tropical beach guy.

46 – Fallbrook (CA). This is a small exurban city on the extreme north end of San Diego County. But those California taxes and living costs are a pain in the neck. The house itself is above the high end of my range, but things can be worked out to squeeze it in. It would add a year to our retirement schedule, which isn’t thrilling. But that house! It’s not huge, but the views are amazing and it’s on five acres. The winters are perfect, and the July high temperature is reasonable. I did happen to notice that the average high temperatures in August and September are 90 degrees, and based on the scoring algorithm it’s not getting penalized for that oddity, so the ranking should probably be a little bit lower. Overall, the cost and taxes are major stumbling blocks, but it seems like one of the best options in southern California, which is an area of great interest for my wife.