Two best days in a boat owners life are the day they buy it, and the day they sell it.
I've heard this for years, I'm not trying to be rude to the boating community at all.
I think this applies to people that buy John boats or heavily used boats. I bought my boat new a few years ago, while there are gotcha's with the money, I've only had one issue with it, some one snuck onto my boat and turned on the lights, when I showed up the battery was dead! (okay maybe the switch was forgotten or something flipped it as we stowed it).
You need to winterize your boat, you need to 'summer-ize' your boat as well, I don't have a space to do this, so I have the dealer do it.
Well you also should acid wash your toons (at least once a year), and you should clean your boat (I do this) at the end of the season, or you can pay to have it done. You can have your boat plastic wrapped or you can store it inside, we go for inside. So we pay for a year round slip, and we pay for winter storage as well. Yes with a slip there is a trailer issues can't just park it at the docks, so we pay to have it stored onsite with the slip.
It is a lot of money, but I'm not crack'n open a motor on the lake and I'm not having headache, its drive down, get on the boat, enjoy the day, park it and drive home. I suspect if we sell the boat it will be with mix feelings. We don't take a lot of family trips, so this is kind of our vacation fund. We do it every weekend and miss it in the winter.
The cold has never really bothered me, not being able to enjoy the warm weather and water does now! Its too close to winter for my liking, I can already feel the somber overtones of 'Winter is coming'.