JES, great post, I am a single guy in my 30’s so the midwest and cold weather do not mix well with me. I am from New England and do not miss the cold after moving to California 20 years ago. I may buy in Oroville in northern California as I work in consulting and travel quite a bit and prices are quite affordable there with perfect weather except for mild winter and some rain in winter and there is a wonderful lake there for boating and hiking and fishing.
My plan is to buy a small place in Oroville then wait til the ball drops in San Diego and buy a second place in north coastal county- most likely a condo since homes will never be super cheap in places like Carlsbad or Encinitas. I like the Solana Beach area as well. Right now I just renewed my lease in Point Loma for another 15 months as I am too busy with travel and work to deal with moving yet.
If I were to move out of state then I would consider places like Austin or Denver as these have fun outdoor activities and decent nightlife for single guys.