I agree with BLJones. When we first got our C25, we were planning to be trailer sailors of sorts. But, from what I had read online at the Catalina owners site (Catalina - Capri - 25s International Association
), the "pros" could rig their boats in about 45 minutes, and taking everything down took about as long. I have two kids; for me, it was a question of how we would keep our kids occupied during that time. Even if we were able to find a marina that let us keep her fully rigged on the trailer, it still would have been tough. It's much nicer to just be able to hop aboard and go (or as close as you get to that on a sailboat). Do you REALLY want to be hauling your boat out while the nasty surprise thunderstorm is closing in on you (or already there)? Those were the kinds of considerations that went through my mind. The cost difference between a wet slip and a "dry slip" (i.e., rigged on a trailer) wasn't that great when I factored all of those things in, and it's not like I was planning to travel a lot with the boat in tow. As they say, YMMV, just providing feedback from someone who has been there (at least somewhat).
There are a boatload (pun intended) of marinas near Deltaville, and the rates seem very reasonable at some of the nice marinas I visited (at least compared to the Northern Chesapeake and Barnegat Bay). I bet you could find a "budget" marina down that way and pay some very good rates. I'm not sure where you're located, but if I lived closer (like back when I lived near DC), I'd consider keeping my boat in that area, or near Solomons.
Most of the boats in my thread really don't need a whole lot of work up front; that's what I had been looking for. I wanted something that might need TLC, but given the impending season, I wanted something that I could drop in the water and get sailing, not something that needed thousands of dollars invested up front. Mind you, I'm not trying to talk you into THOSE specific boats, just letting you know that they are out there.