A big question is your kids? If so, you want to be very careful where you buy a house because the schools and the friends they'll make.
We came down from the Jersey Shore two years ago - waterfront with 10k lift. We now keep our boat at a high and dry.
We found "decent" waterfront to be very expensive and throw in taxes and the fact that you will be in the Citizens "aka catastrophe" insurance more than likely. Make sure you get the full picture on what the cost will be.
We live in a place called Lansbrook which is north of Clearwater about 5 miles right on Lake Tarpon which is a pretty big lake and about a 20 minute drive to the beach or marina.
I have the typical familiy unit so if that's your situation you might want to make sure you check out the people giving you advice to see if they have the same outlook as you... boating aside. We took five trips down to check out the place and still had quite the education after the move.
I like Tampa because it's not as nuts as the East Coast (or crowded), property is still somewhat reasonable, you have a major city (at least by Florida standards), and some of the best beaches you'll find anywhere. Life is much easier without kids - so are the choices. It is much more a boater friendly laid back atmosphere too.
Best move of our life - we love the Tampa.