Our dock rent runs between $700 and $800 a month, so say $4,500 for six months. That include the dock, electricity, cable TV, and one pump out.
Our boat carries 800 gallons of diesel, and we have about 700 gallons in it. We burn 5 gallons an hour at 8 knots, so we can travel about 1,100 miles. We're 400 miles from the Bahamas, so we'd have enough to get there, spend the winter running the generator (1 gallon an hour, two hours a day, 360 gallons), and return. I could also just run the smaller 7 1/2 KW generator, which would burn half the fuel, since we wouldn't be running the heat or A/C much.
Ocean Petroleum here in Brunswick sells diesel at $3.76 a gallon, so say we used 800 gallons for six months, it would cost us $3,000 to live on the hook.
But I think if I was going to live on the hook, I'd take the Whaler off the flybridge and cover the upper deck with solar panels.