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First of all, remember that no deal is too good to pass up.

Will the boat be in or out of the water? You'll want to see it out of the water if you are concerned about blisters.

I would definitely plan on this being your first look, and if you like the looks of the boat either hire a surveyor or, at the very least, come back with an experienced boat owner.

Check out this sailnet thread.
 

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I don't know your personality or budget, but I would also caution you about getting wrapped around the axle over the 10,000 things that can be wrong with a boat. Read over the inspection tips, get comfortable with the level of financial risk you are taking (is this entertainment money, vacation money, or retirement money you are spending?), and find a boat that you like, understanding that it will require maintenance and probably at least some level of repair.

Good luck!
 

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Well fiancé and I are elementary school teachers, so we do ok between the two of us, but our budget is nothing huge.
I wasn't really referring to the amount of money as much as the relative expense compared to the rest of your finances.

We got a 27-foot boat for very little money (less than $5k) a few years ago, in the Baltimore area. My wife and I agreed that we would give it two years to see if we wanted to continue with the ongoing expenses. We just finished our third year, and although we didn't get out much this summer, we still enjoy having a boat. The important thing is, we are able to take this as a "see what happens" type of thing because we did not take a big financial risk. Yet we still got a sound boat that did not require any major repairs, and sails well, and has a clean interior in nice enough shape for overnighting with our two boys.
 
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