ASA and PSIA Instructor
Join Date: Apr 2000
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Nice turn of events, sounds like you are moving to sail heaven (but no skiing...).
On the deck repair, I'm sure you can muscle through whatever needs to be done to get a solid deck - the concern I'd offer is how difficult a job it will be do do a quality job on painting a deck. I've painted hulls before - it can be hard to get a great finish - I think a deck is much more difficult to do, both due to the number of corners and panels, and the fact that the end result is always right under your eyes, subject to continual inspection. If the boat is otherwise in excellent condition, anthing else than a professional-looking paint job may materially lessen the value of the boat, and perhaps your enjoyment. Your call, but I think the bar is much higher than if you were just painting the topsides...
Another thought is that living on a 2-27 ain't much living. Have you considering trying to use the move as an opportunity to move up - maybe you can sell the 27 and get some money out of the company for "loss of value" due to a rushed sale...then put the money into something a little bigger, even a 33 would provide a lot more space, perhaps some amenities like hot water, etc. If you are living aboard it can be important to have adequate room for the inevitable guests. Consider a loan if necessary...