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Looking at a few boat's needing a few more opinions. The older the better.
I purchased my "new" boat (an '81 Catalina 27) 2½ years ago. I got what I think was a good deal, $6,000 with new sails & outboard (1½ years old for both). The only money I have put into the boat was new batteries (and several upgrades I have made, but not necessary). I would steer clear of wooden boats unless you have expertise in that area. I would stick to fiberglass, and I would plan on spending money to "fix it up" to meet your needs. I was lucky, but repairs can be costly. Also, you should consider a surveyor, to give you an accurate understanding of the boat's condition.Looking at a few boat's needing a few more opinions. The older the better.
Where will you be cruising? How many people on the boat, most of the time?looking for a cruiser for sure strictly sail no huge power, and older because it has a history behind it,and heart.
I take out my C-25 all the time, and my 12" Escape Captiva has sat in the garage all season. Easier to hank on a jib and throw off lines than tow the boat and launch it.The smaller the better. I have done a few 3 day cruises on my 24, but I take my dinghy out every day. It's true, the amount of use a boat gets is inversely related to it's length.
I think you'd be more worried about seaworthiness, current shape and ease of maintenance than a history. It's is true that older boats can hold together well for a long time if they have been well maintained. Mine is a 79 and I found out this weekend that I'm the 6th owner. ( I ran into the FO and the FFO on the dock last weekend.)looking for a cruiser for sure strictly sail no huge power, and older because it has a history behind it,and heart.