There isn't anything inherently wrong with wintering in the water in an area with not much ice, assuming the boat, including its seacocks, are properly winterized.
Thick ice is said to squeeze the hull, which may damage things. Also, when it melts, the big ice sheets
have the tendency to take moorings and docks with it. Doubt this is a problem in your area.
Many in NYC
winter in the water on some alternating schedule. One year in, one year out. Ice is rarely a problem. One really should come out at least once every other year to get painted.
The issue I see as necessary to wintering in the water is making it out to your boat every few weeks to check on it. My boat is out on a mooring
, so that would involve me rowing, which would not be fun and could be dangerous.
Agreed with others that $2,500 sounds high. I pay slightly less than $2,000 for my 38' in NYC