#36 through 40. See the picture for details and scoring. (I really wish I could format tables in the regular text, by the way.)
36 – Hot Springs (AR)
https://www.realtor.com/realestatean...-75244?view=qv
37 – Eugene (OR)
https://www.realtor.com/realestatean...-15424?view=qv
38 – Tulsa (OK)
https://www.realtor.com/realestatean...-53837?view=qv
39 – Orange (CA)
https://www.realtor.com/realestatean...-70876?view=qv
40 – Cocoa Beach (FL)
https://www.realtor.com/realestatean...-79044?view=qv
Summary (starting from the bottom)
Cocoa Beach (FL) – This is a very interesting house. Check out the pictures in the link and click on the little map. It’s a corner lot with canals on two sides, and I could watch the rockets take off from Cape Canaveral. The house is a combination of really interesting and nice features and really bad and dated features, so it would take some work. But Cocoa Beach is really affordable (pushes retirement up by 1.5 years) and my wife would never see snow again. Hot and humid summers, of course, but we would live on an island. An island! I could actually do this.
Orange (CA) – Taxes and cost of living are unavoidable hurdles in California. This house isn’t fancy (other than the pool, which is pretty fancy), but it’s a nice house in a good location. No snow, tolerable summers, and a good general location make this a contender. But it’s a year longer to retirement to do it, which is a big downside. My wife may like the tradeoff, but I don't.
Tulsa (OK) – Okay, check out this house. It's awesome. It’s 3,800 square feet on 1.4 acres in the middle of the city, and the house is very interesting architecturally. The pool looks like a Hugh Hefner grotto, too. I'd probably have every Instagram model in Tulsa lounging topless at poolside taking selfies. The winter is tolerable with 1/10th of our Denver snow, though the summer is 5 degrees hotter with a little more humidity. It’s a higher-cost house at the extreme upper end of my price band, though, so even though it’s still more affordable than staying in place, it would only cut 6 months off of my retirement schedule. I'm not sure it's a good tradeoff. But that house...
Eugene (OR) – I’m surprised that this falls into the “affordable” side of the ledger, but it does. The climate is really nice, with relatively mild winters and summers, though there is a fair amount of humidity. The only downside is that housing is expensive, so the sample house is nice but relatively small at 1,600 square feet. Eugene is a much stronger contender than I would have expected, though, since it’s got a lot of above-average attributes.
Hot Springs (AR) – You get a lot of house for your money in Hot Springs. The overall price is at the low end of my price band, and check out the outdoor kitchen. When I visited there last year, I found the town and area to be attractive and appealing. The winters are somewhat mild, though the summer looks like it would be notably worse than Denver (higher temp and higher humidity). The low costs make this competitive, but having lived in Arkansas once I would want to screen in all of the outside areas to keep mosquitos from eating me. This may be a long shot despite its attractiveness, because I don't like mosquitos.