Re: In water for the winter
Boston Harbor proper doesn't really freeze, but you can bet most of the protected harbors the marinas are in do. Green Harbor just south where I boat froze up solid, as did Dorchester Yacht Club (Boston)
BUT that said, people leave their boats in year round here all the time. I can't tell you what precautions they take but lobstering certainly doesn't stop.
I think the biggest concern I would have is snow buildup. if scuppers and drains block up from ice or debris it won;t take long to get top heavy. I'd be checking on this thing every few days. Battery dies and no bilge pump, especially with no shore power for backup, would cause me more heartburn than it's worth.
I understand not getting it out today, but we still have another month or two of boating (my season is kind of just getting started here!

). He can't plan to have it pulled and stored in the next month or two? I mean you re going to bear the cost of winterizaton in the water or out, so the difference is a haul out and a cheap place to lay it up if you don't have the space. It's doubtful we will have any extended freezing temps before Xmas so draining the block down would probably suffice to combat a freak hard freeze, but there is more to winterizing than that.
M