Jacksonville is very interesting. Not a bad place to travel to every now and then either. Thanks for the tip!
Re:Chicago -
I was born and raised here and I've been watching prices for about 20 years. At a macro level, it's a so-so market, though you can find deals if you are alert to new developments.
Prices here follow population and job growth. The best long-term appreciation is likely going to be seen at the core as density is increasing pretty rapidly with the demolition of Cabrini Green, the high school being built in River North, rapid commercialization and the new TOD zones on the west side. Lots of tech jobs being created here as well. I think the near north side is going to resemble Manhattan in the next 20 years. So very solid, but I have a big chunk of my portfolio here already.
I have no interest in the south side or suburbs due to lower potential for appreciation, outrageous property taxes in certain burbs and risk of decline in certain areas. Also, I'm looking to diversify my metro exposure.