Here are my #71 to 75 rankings. I actually screwed up on Jackson, WY, so it's ranked too high. It should be #81. (In my housing grades I accidentally graded Jackson, CA.) But whatever, it's here now. If you're scoring at home, move it down six spots.
Redding (CA)
https://www.realtor.com/realestatean...-71296?view=qv
Warsaw (MO)
https://www.realtor.com/realestatean...-35676?view=qv
Durango (CO)
https://www.realtor.com/realestatean...-43601?view=qv
Hilo (HI)
https://www.realtor.com/realestatean...-37532?view=qv
Jackson (WY)
https://www.realtor.com/realestatean...-24493?view=qv
Summary:
Redding – North central California so I thought it might have a nice climate. However, a warmer winter is the only advantage. Higher taxes mean I’d have to work a little longer to retire there, and the summers are pretty hot. It’s a bit more humid than Denver. It's okay on the housing selection, though.
Warsaw – It’s on one of the big Corps of Engineer lakes so I thought it might be nice. We drove through it once and thought it was kind of charming. Pretty much the same story as Redding, but it’s more affordable and would cut a year off my retirement timeline. The downsides compared to Redding are that it’s more humid and is a pretty small town relative to health care, restaurants, etc.
Durango – It’s a wash with staying in Denver. The climate is nearly identical and the affordability is the same. But we’d likely have a slightly smaller house if we moved. This is really pretty neutral so it’s more whether you’d want to live in Denver or Durango, each of which has their advantages.
Hilo – Very nice climate in Hilo, other than humidity. Pleasant winters and 8 degrees cooler than Denver in summer. You get a whole lot of rain, but big deal. The only problem is that the houses have that “beat up by the tropics” feel. You can’t get a non-fixer-upper in my price range, which would then add a lot of cost. It's interesting that my retirement savings would last longer there than in Denver, though. If the housing stock was more appealing, this could be a contender.
Jackson (WY) – Housing affordability is ridiculous, so it's a no-go from the start You'd also have notably colder winters than Denver with a lot more snow, which is not what we’re targeting. It's a very cool town, though. There's a reason why it's expensive.