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Like Eric said, what are your capabilities and what do you enjoy? I absolutely love working on my boat, even wearing a Tyvek "bunny suit" and grinding fiberglass all day. The material cost for repairing blisters is probably only a couple of hundred bucks but, if you are paying a yard to do it the labor will kill you. I am also fortunate to have a place at home to store and work on my boat so It is easier to do big projects a little at a time.
Whoever said that owning a boat makes financial sense? If you like your boat and plan to keep her for a long time make the investment. A new set of basic cruising sails is only about $1500.00, I know people that spend that kind of $$ fixing their sand rails after 1 weekend at the dunes, sails last for years.
If you have been considering moving on to a different boat anyhow sell her cheaply to someone who will do the necessary repairs and buy a boat in better shape.
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