One thing I will say. My sailboat is less of a money pit than any personal watercraft or power boat that I've had. The other thing is its always a family affair. While I'm the mechanical one in the family, my wife is always good with cleaning up the messes I'm making while working. My 13 year old son is learning and has become my mast monkey, while being a small enough build to get into places I can get into but have difficulty getting my tubby butt out of. Even my 10 year old gets in on things. He's small, great and squeezing into small areas so he can hand me tools, screws, nuts, bolts etc. There is always something that needs to be done.
The most enjoyable anniversary trip I had in 16 years of marriage was on that boat

Panta Rei is dead on, its an investment in time and money, but the return is worth it in my opinion. Just make sure you don't have anything major wrong with the boat. Sounds like you are getting a deal (dock fees?) because they want to be done with it?
As an aside, I'm also happy to provide shots of any modifications I've made to my boat. A lot had been done to it before I got it and I've done alot to it afterward and still going. Running joke in my Marina is that I've got the most ridiculously over equipped 28 in the marina. Personally I think the guys in the 34 plus boats are just jealous that I have AC and heat
