no easy answers
For sure, take the boat out of the water. I left mine in once and regretted it. I spent the entire winter worrying about the boat.I shrinkwrap mine, but it's expensive and may not make much difference. Face it, you leave your boat out in the weather during the season, what difference does it make when it's cold outside? There are lots of horror stories about getting snow & ice in the cockpit, but I think they are mostly urban legends

I still wrap it, but I have my doubts.Some people shrinkwrap their own boat. It's supposedly not that difficult and the only special tool required is a (big) heat gun.There's a place in Branford that will store your boat indoors. It's expensive, but some swear by it. If Brewers will just raise their rates one more time, I'll be trying to garage mine, too.I have the mast unstepped. I like to inspect the rigging up close and have the riggers inspect it, too. My hope is that the swage will break as they are stepping/unstepping the mast, not when I tack the boat. Lots of people leave theirs on, though.I just read Steve's answer, and I think it's about the best boiling down of options I've seen. I would add the obvious, that indoor storage would be the ticket if you had any kind of off-season project plans.