Long distance: I don't know which city to pick

[Teho Kim]

I'm about halfway done with David Greene's long distance REI book. The book doesn't cover on how to pick the city you want to invest in.

I'm leaning towards Florida, particularly the area in between and including Orlando and Tampa. This is really just a whim however, based on that I could see myself retiring there; and a small chance that my work can take me there in several years time. Is this enough justification to just go with it?

How should I go about picking a city? Appreciate any and all insights.