Wood doesn't scare me, but neglect hidden by cosmetics does. My first boat was a Mirror dinghy, so I cut my teeth on wood maintenance, wood repair, and the importance of not getting behind the maintenance curve.
Then, apparently i got stupid.
My next boat was a 27' Owens cruiser, with a fresh paint job, and suspiciously, the only painted transom in the entire marina. Said transom promptly attempted to exit the boat when hauled for winter after my first and last season of ownership.
Between wives I bought and lived aboard a CC Sea Skiff- fast, thirsty, comfy and solid, and I realized how little maintenance there is to do when you are not playing catch-up.
And last fall i found another one, in need of a new steward. You don't own a wooden boat- you're simply the caretaker, maintaining the legacy.
Funny thing about wooden boats is that you never find the right boat- it finds you, and when it does, all of your rationalizations and rules of boat ownership fly out the window. If she is the right boat, you WILL resuscitate her and love every minute and every dollar spent, and there are few fiberglass boats that make me feel the same way.