Ft. Myers vs. Naples vs. Clearwater

First of all my apologies for beating a dead horse here cuz I know that you Florida guys have been asked these questions a thousand times. My wife and I are in Spring Hill, Fl. right now for spring break w/ the kids and another couple. We decided to try the VRBO.com and got a great house for less than $1K/wk. Anyway, we are looking to buy a 2nd home here on the west coast and we want to be in Clearwater or south of that. We would probably come down from Michigan a half dozen times per winter and try to rent it the rest of the time on VRBO. I have poured through the archives here and read all of the discussions on these areas and I know that Naples has a lot of older folk but is very unique and clean, and frankly that is what we are looking for the most, as well as nice beaches, a cultural district and as few "booger eaters" as possible, like we've seen here in Spring Hill. Some have said that the "sidewalks roll up at 9 p.m.", but others have said that there are a few places that are fun for the "younger" crowd. We like to have fun, but are not looking for a "cancun" type atmosphere where waiters are pouring shots down your throat. We are looking for a foreclosure or fire sale in the $150K range. We want a 3-4 bedroom/2 bath w/ a pool within 5 miles of the ocean. My questions are: What could we expect in property taxes on something like this? I am guessing about $6k/yr? Insurance maybe $2500/yr? What about insects in these areas? Would we need a net around the back yard? What would push me toward one of these 3 cities vs. the other 2 mentioned? Anyone know anyone who rents in the Naples to Clearwater area on VRBO or other sources? If so, how often are they rented? Again, sorry for the re-hash of these types of questions, but this is a very important decision for us. Thanks!