re: Aynone here have a sail boat or know much about them?

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what are the main worries with buying a 25+ year old sail boat?

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- hull integrity: are there any soft spots/cracks in the fiberglass? is the paint/gel coat still there or has it faded away, leaving the fiberglass exposed?
- sail quality/rigging: is everything I need to go out sailing today on the boat/in working order? are the sails torn/worn/tattered? is the rigging in working order?
- motor: does this boat have a motor? does it work?

can't think of anything else off the top of my head but I am sure I am missing something.

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many of the ones I have seen have inboards, is that preferrable?

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- if it works good, then yes IMO. All boats I have had had outboards, however, I think boats don't look as good with an outboard hanging off the stern.
- outboards are easier to maintain, inboards are more convenient and look better.

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The one you linked is 30', is there a preferrable length? Have seen a few 26 and 27 footers I am interested in also.

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30 is just the neighborhood of the next boat I will get, so that was a little biased of me . 26' or 27' would be fine. Size depends on what you want to do with the boat/how many people you want to have on board, and how comfortable you want guests to be.

I had a 22 footer that I just got rid of back in May. I regularly had 5-6 people in addition to myself onboard. It was a little tight for space sometimes but we managed.