Didn't read all the posts, but you and I are very similar. After college my (now ex) wife lived in a Travel Trailer and went wherever we wanted to try. Here is where I have lived:
New Orleans (just outside NO in Slidell). Fantastic town. Airport is a big destination so its cheap and flies everywhere, but somehow small. I hate huge airports; long security lines and more delays. The vibe is relatively conservative on the political spectrum, but southern LA conservatives are pretty liberal by comparison. Close to one of my favorite towns.
Los Angeles. Massive airport that is a pain, but you're right close to Burbank and Long Beach airports which are both small but fly everywhere. Weather is amazing, tons to do, but you have to love cities. Getting out of the city can be a 2 hour ordeal and then you're just in desert for two hours.
Tampa/St. Pete. Nice town. Outskirts are a wee bit depressed. I lived there when I was in my 20s, so I didn't really appreciate that the average age there was "deceased"
Austin TX. Super sweet town. Cost of living was a tad high, but no income tax. Once a year you paid a consolidated school, property, municipal tax to the county tax office and they took care of everything else. One check, and not a big one at that. Most of the town is super liberal, but 5 miles out of town is all Trump signs. I loved Austin. Their motto is "keep austin weird." That pretty much sums it up. Also a great airport that flies everywhere but isn't big and annoying.
Pittsburgh. Not my kind of town. I really hated Pittsburgh. No offense to any of you who live there, but it is a depressing, grey, angry, complacent place for a guy like me. It is getting better, but not fast enough for me. I prefer progressive, hopeful, happy, enlightened. Pittsburgh is one of those places where the secret to happiness is lowering your standards to the point where they're already met. Just don't have any dreams of bettering yourself and you'll never be disappointed.
Kalispell MT. For a small town, this place really held my interest. I was only there for a short time but so lovely. Progressive, fun, and one of the most picturesque places on the planet. Regional airport that could get you to Billings or Boise.
Evansville IN. What a cute city. Temperatures can be a little extreme both ways but not bad. Good, small airport.
Places I've visited and liked:
Asheville NC. Gem of the south. I need a little bigger city to keep me happy. When I was in Asheville I found it to be remarkably vacant, but I was there during the first week of January. It just seemed like there weren't very many people there. On a wednesday I recall driving downtown and I was the only person on some streets. Strange.
Santa Fe NM. Just visit. Its smaller than you think but so quaint and neat.
Places I really don't like:
Houston. The whole town smells like you're inside a crude oil tank. The skyline is smoking towers. One time I was there it was 98 degrees and foggy. Not just hazy. Foggy.
Dallas. Yawn. Good for food, banking, and oil companies.
Miami. I don't like it but part of it is my fault. I grew up worshipping the show Miami Vice so I saw it as this glamorous, fun, party town. Its really just a town of old Manhattanites. I did really appreciate the Cuban influence.
Chicago. Nice to visit, wouldn't like living there.