I live in Boston and over the past thirty years I have usually covered my boat. Several years I did not cover the boat and there were no ill effects, if the boat is water tight, which generally means the mast is removed. You do need a strategy for keeping ice from accumulating in the cockpit, as may occur with several cycles of freeze/thaw where the cockpit drains may become blocked. Visiting the boat after storms can deal with this risk.
I do think annual shrinkwrapping is too expensive, plus last year the crew put it up in a way that took down four stanchions in the winter. So I am trying something new this year - I saved the shrinkwrap frame and have cut a large plastic tarp to fit from the frame to the slotted toerail. I am having the cover hemmed and I'll add grommets, giving me a custom cover for the deck. In addition to being reuseable, it should shed snow completely, and leaves the painted hull uncovered and free of tiedown lines, and is costing less than one year of shrinkwrap. We'll see.