If you like cheap and great community, check out Hernando Beach on the gulf. Lots of affordable housing for sale with dock on canals with direct access to the gulf. Quiet neighborhoods with LOTS of great people who are passionate about the water. My old neighbor moved over there and he and his neighbor builds boats for fun and are constantly out on the water.
You're about an hour away from Tampa for some city time, and right near Weeki Wachee springs which is a great day trip if you like freshwater springs.
I live on the east coast, and around here your best bet is Hobe Sound, Stuart, or PSL. All will be a bit more expensive than the gulf and dock space can be tricky on a tight budget if you have a (larger) boat as you're limited by a lot of low bridges in PSL. Jupiter and WPB are pricey but absolutely great fishing, and good luck finding a slip at a decent rate.