We've been going to FL pretty much every year for the last 15+ years on vacation, mostly the Orlando area. We have gone a few times to the Gulf coast (Sanibel/Ft. Myers/etc) and really like that type of area.
We love being on the water... our main summer activity is boating. I have a 23' boat, and it would be fine for closer-to-shore trips in good weather, which is fine with me. Unfortunately, we get maybe 3 months of great weather here in PA. And we lose some of those weekends to other commitments, thunderstorms, etc. I see that housing prices there are still depressed... I have seen 3BR/2BA/2G houses, on a canal, with a boat lift going for under $300k, with 10 minute Gulf access in SW FL. That would be ideal for us.
The major hurdle is employment prospects. I am a .NET software/web developer with 10+ years experience. I work remote for my current company, so I can live anywhere that has internet access. I have no plans to leave this job, and it is a HUGE benefit for me to be able to live anywhere I want... such as the SW coast of FL.
What I'm worried about is that, although I'm pretty confident in the stability of my company, I don't want to put all my eggs in that basket. I don't want to find a beautiful dream home on the Gulf and find a few years later that my current company downsizes, outsources, or anything similar that would require me to find new employment... and Tampa is 200+ miles away. Buying an "isolated" home based on my company is akin to putting all my retirement portfolio in company stock, IMO.
So, I'm wondering if there are any areas on the Gulf coast with some hotbeds of IT activity, so I can have a fallback plan in case of the longshot event of my current company going away.
I'm also somewhat concerned with flood insurance rates, but I guess we'll cross that bridge when we come to it.