I am just finishing up a project
such as you mention here. Ours is a Cal
2-29, fiberglass with enough wood to make it look nice, but not eat all my time up maintaining it.
Even a boat that would seem to be ready to go will in all likelyhood need quite a bit of work to bring it to the condition that you really want. Of course, that would be your personal choice as to what condition you really want a boat. Some want a show boat that they never have a chance to sail, others want a boat that they do very little maintenance
and just sail until it falls apart. The vast majority I think are somewhere in between.
I am always amazed at how much I spend on just the seemingly little things as Paul mentions. But in the end, I would never trade
our sailboat for a power boat
. I love sailing far more than driving a power boat. I have owned several of both up to 40'.
One of my all time favorites was a little day sailer - a McGregor Venture of Newport cutter
rigged trailer sailer. Very light - not overly sturdy ( I did sail it in the ocean in the PNW - but only on carefully chosen days) but a joy to sail if I was only going to be out for a few hours or a day at a time. What I really liked was that I did not have to leave it at a slip in one place - I could trailer it to any lake or bay that I wanted to. This is not a recommendation for McGregors - just that I liked the one I had. I also had a McGregor Venture 21 - I liked the Venture of Newport
The only thing I would really say is don't buy any boat sight unseen. Don't buy an "Ebay boat" unless you can go and carefully look it over first.