Yes you should cover it somehow over the winter. We get too many freeze / thaw cycles that gets water into everywhere then freezes and will do damage.
Shrink wrap is the most expensive if you have the marina do the work, but easiest. You don't have to do the work, but current rates are around $20 per ft, so makes it $ 600- 700 per year. You can do shrink wrap yourself, but equipment is more expensive and takes some technique to get it right. Get it wrong and it will cost you even more. But, lots of people do it themselves, all depends on your capabilities and available time. Tarping / wrapping will take at least one weekend the first time, then down to one day once you know what you're doing.
Custom tarps will run $2-3,000 depending on if you need frame etc. Check Genco for one, I think they have templates for most boats.
Econo tarp is from TSC ( not sure if you have one near you ) I used a hay bale tarp, heavy silver ones from TSC and has lasted 4 seasons, $ 200. I made a ridge frame from 2x4's and made the tarp steep and and very tight so the snow does not accumilate. Has worked without any problems. Tarp is on its last legs so will be time for a new one. For comparison, custom tarps should give you 10 yrs. or more.
As far as timing..... I'm usually still in the water over Thanksgiving and then winterize / tarp late Oct. / early Nov. Season is too short as it is....
) This has worked well for the last 20 years+
