I don't know much about either boat, but can offer some info on the sailing Tampa Bay. Shallow draft is definitely a plus, and you want a boat that performs well in light air. I find many more days with wind around 5 knots than 15 knots.
As far as Davis Islands Races, they are for for the Davis Islands Yacht Club. They are open to the public, but you have to sail someone's boat who belings to the club. You cannot sail your own boat without being a member (which to my knowledge involves a lenghty application process and a significant amount of $$$).
One thing to consider is docking. Boat slips in Tampa are expensive and hard to come by. Most of the marinas have long wait lists, some in excess of 10 years. I made the mistake of buying a boat, before I had a place to keep it, which turned out to be a big issue. Definitely look into this before you buy.
As far as the boats, Mid 20's is a perfect size for daysailing in the Tampa Bay. I would make sure the boat has a small cabin. The women really appreciate it. Also it allows weekent trips to places like Egmont Key. There are a lot of boats around in your size and price range.
Good luck with your search.