Well after many months of should we or shouldn't, the movers are set and I will be there in early October.  Flying down early in September to secure a rental for the first year, then back to ownership.  Any suggestions that you guys would like to make on anything from where the desirable areas are to where we shouldn't look would be really appreciated.  You can either tie them to this post, or pm me, sort of whatever blows your skirt up.  
Thanks in advance, to all of you that respond.  The Naples market and the Chicago market are quite different, if anyone would like to share what you perceive to be those difference would, again, be really appreciated.
Looking to learn from a composite of the best and most active in the hobby.
Dwayne