First of all, this is a very informative thread and I think it is great that people have thoughtfully contributed in such a helpful manner. Hopefully I can leverage some of this.
First, I am a FL native. I grew up in a small town in central FL which had few redeeming qualities other than its proximity to other areas. When I went to college I moved to Jacksonville and stayed for about 10 years. I thought Jax was great- anything beat where I was before.
A couple of years ago we moved to Kauai. For me there has been no higher quality of life that I could imagine, and I have a very interesting job to boot. However for family and cost-of-living reasons we will eventually return to FL. At this point the thought of moving back to Jax is not a pleasant one.
When the time comes, I may have a career opportunity in the St. Pete/Largo area with my existing company. I am intrigued with the thought of living in this area (instead of Jax) for a variety of reasons. Compared to Jax, the beaches are much nicer, the winters are more tolerable (ok, I have THIN blood), more natural beauty&waterfront areas, etc. There appear to be various communities that would be within commute distance, most all of which have been outlined well in this thread.
First, schools: my wife and I are both products of the FL public school system but of course our experience is dated at this point. Our experiences were mixed but we weren't in the best schools. We never thought we'd consider private schools but all kinds of things change when you have a kid- so that option is on the table. I would be interested to here stories from parents who live in this area of FL- how did you make your decisions, how are your kids doing, etc.?
Second, are there areas in commuting distance to Largo where one could have a new house built? Either in a subdivision or vacant lot for sale? If so, where are some places to look? We would basically be looking at spending 400K or less for land and home, and don't want a big yard. I guess this makes us candidates for a "cookie cutter subdivison". Living in a newer area that has reasonable HOA rules has some appeal to us, although this concept can lose its appeal quickly if it becomes too overdone or too "fake".
Third, are home prices really on their way down? Listening to the way the media is portraying the current real estate situation, a person would think they could buy a beach front house for 50K or something

However to be honest, looking at things from afar (online MLS searches and such), I haven't seen much change in advertised prices in the FL locations I've browsed.
Thanks a lot, in advance.