I'm on the west coast of FL and just bought a trailer-sailor. I have a slip behind my house but there is one bridge to the harbor/gulf, so if I ever wanted to bring it home by water it needed a folding mast. The harbor can get shallow in some areas on the way to the gulf, so a swing keel appealed to me. If I need to bottom paint or do maintenance I can trailer it to my driveway. I'm going to learn to sail on her, and will probably beat it up a bit so I wanted something cheap.
So, I decided on a "trailer-sailor" for more than just $$ and storage reasons. If
I find that I LOVE sailing but hate the rigging I can then at least justify getting a bigger boat and pay for "storage", haul outs, bottom cleanings etc. If I decide sailing is not for me, no big deal. A boat on a trailer is MUCH easier to sell than a moored neglected boat with barnacles on the bottom.
I got a great deal on the boat, much less than what you want to spend...I figure I can learn to sail, beat the hell out of it and then STILL double my money when it comes time to sell, whether that be next week or in 10 years. I like to start small and work my way up, making money on the way.
FWIW, it takes me a few minutes tops to put up the mast, another 30 seconds to drop the keel. Fiddling with the sails can be a bit of a pain but really, how much extra time does it take to be ready to sail than on a moored boat? And if you do decide the trailering/rigging is too much work you can still moor/dock it....but at least you have a trailer to get it out to work on, or if a storm is coming. You think $400 a month is a lot? Wait till you ask them to haul the boat out for you with the crane, and put it back in....with a hurricane coming and everyone trying to get pulled out on the same day.
Like Frog said above a trailer will allow you to sail in different places. If I decide I want to check out Tampa bay or wherever, no problem, just trailer it up there. It would take 2 days to get there by sail
And the Keys........yeah, i will be trailering it down there!