I sorta agree with C&C. I'm formulating a theory that most old boat(and land vehicle dreams) takes two owners. One to fix it up, and one to enjoy the fruits of the labor... next time around I'm going to try to be the 2nd :-).
To be fair I've always imagined working at the carnival to be more interesting than wandering around overspending on silly plastic trinkets. The machines at the carnival are COOL.
So long as you get what you need out of the dream, whatever part of it is yours, I'd say it's a win.
I'm in the halfway department, I'm halfway through a refit, and I still plan to sail her, but I've swung a bit to CnCs side, some of the magic is gone, I've found myself looking at trawlers even recently... but hopefully I finish the refit before it all runs out. Having spent a lot of time fixing other's boats now, I've learned that many(most?) owners haven't got a bloody clue when it comes to boats, which is fine.
My boat's previous owners lived aboard for months, and some of the things I found not resolved told me they hadn't applied their faculties to the boat, I know they were smart enough people.
Also, caveat surveyor. Trusting one of those to use their eyes, or be honest can cost a lot in terms of blood sweat and tears, not to mention money.
Next time I'm trying to buy one that someone else has taken the hit on, where the magic wore out but that next time is far away. When I get to sail mine around the bay sometime soon I'll know if I've crossed the line that CnC did, I like to think I'm still toeing it, learning about the boat, while not entirely losing the magic.
Quality, older and well refit is the best deal, the trick is to find that, barring buying a boat that someone like Chris has done up, find one where whatever is causing them to sell it is something you can handle comfortably. For example I'll take a boat in need of electrical, but not one in need of rigging :-)
It's an inaccurate generalization. In the past 12 years, I have done a lot of work on the two keel boats I've owned. The one would have been a complete restoration if it hadn't been for other factors. The one I own now was in the "project" category. I loved working on them both and loved sailing them both. Having said that, I am happy to be now reaching the point on No. 2 that I am more maintaining systems than rebuilding them - it has already paid dividends in more sailing time, something I sorely missed for the first few years of intense work. I have definitely met people who like working on boats more than they like sailing them, and people who hate working on boats but love sailing them.
There's no zero sum game here, but a spectrum, from 1 to 10. On that scale, I'm probably a five. I have known plenty of fives.
I think this either/or is a canard for folks trying to rationalize their extreme proclivities.