There are two schools of thought in getting an older boat. One is to look for one that has been constantly upgraded and needs minimal work, but may not be setup the way you would like it. The other is to look at a boat that has been well-maintained but not upgraded, and then spend the money on setting it up the way you want it. A lot of this depends on your time frame—how long are you going to keep the boat. If it is for the long-haul, the second route is probably better than the first.
As Don Casey points out in This Old Boat, many boat owners buy a first boat, keep it for a relatively short time period, and after learning what they like, dislike, what they want and need, they go out and buy a second boat—which they may keep for decades. If that is the scenario you're looking at...by all means get a boat with a good basic skeleton, and then kit it out the way you want.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.