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I started yacht sailing with a club that existed mainly to own half a dozen yachts which it chartered to its members at cost. So a half-way house between what you are looking at and conventional chartering. The charters were divided between skippered training sessions by instructors in the club, skippered racing, an annual long-distance cruise (picking up and dropping members along the way), and short bare-boat charters by members.
Just a couple of charters per annum was sufficient to make it very good value for money, though I usually got in four or five. It was a first-class method of gaining experience prior to buying. There was as Sailingdog suggests, an issue about maintenance. We paid for a club bosun to organise this and keep it under control, luckily we had a fairly dedicated core of members willing to help. With the yachts in use 48 weeks a year, it was occasionally an issue. But even so, it worked well.
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