I probably live in a pretty low-cost boating area, but still -- we pay about $2000 to have it hauled, winterized, and stored mid-October through May 1, then another $400 to have it re-launched in the spring. I could reduce that cost a little by winterizing myself, but then if I miss something and lines freeze and crack (or something worse) it's solely my headache if I've done it myself. If we have the marina do it, it's their headache instead, so to some degree I'm buying winterization peace of mind. We have a new (to us), bigger boat this year and so for the first time we're having it shrink-wrapped. We'll probably have a winter cover custom made next season, we just ran out of time this summer. Long term I just don't see how shrink-wrapping makes financial sense, throwing all that money in the dumpster each spring.
My dad lives in Stuart, FL and we've talked about the year-round thing. Of course we don't pay slip rent for the winter up here in SD, so it may be a financial wash overall. Still, it sure would be nice to have a drink on the back deck in January -- instead of shoveling a path through the snow in the storage yard to check the boat.