No doubt your record is impressive. However I prefer to look at my boat not from a strict financial perspective. The upgrades I make are for my benefit and enjoyment and if they enhance the resale value of the boat, then that's a bonus. What keeps me in check is that I'm inherently cheap which does not stop me from admiring the Alberg 30 down the dock that has had a bazillion bucks spent on it.I think I pretty much proved you wrong that a sailboat can indeed be a good investment, & that you can not only make money on a wise investment, but I actually doubled my initial investment on all 3 of my past boats. I think that's a pretty impressive track record. If you start with a bad boat to begin with that isn't very desirable, attractive, or sea worthy, then you'll never recoup your investment. Having "an eye for it" starts with a good, sound investment. A 1972 Catalina 22 is only worth about $3,500 to 5k tops.
If somebody dumps 40k into a lil boat like that, then they are just throwing their money away. When you consider what 40k can buy in a good, classic sailboat then it is even more of a waste, & is poor judgement. Plus you could easily buy a brand new C 22 for less then this, or a very nice 90s era C 30. I would be embarressed to admit that I had spent 40k on an old C 22. The only thing positive to walk away with is that when you document what you've already spent, at some point common sense would hopefully kick in & give you a wake up call. This should be an example to everyone of what not to do with your money. Its great to have a hobby, but this guy reminds me of the saying, "you can polish a turd, but it will still look like a turd." On the other hand, if you spend a few bucks more to buy something decent, then it will cost less to maintain & likely be a whole lot more enjoyable at the end of the day. My 2 cents.
My point is that it takes all kinds and all sorts of different points of view. It's a hobby after all and the point is to enjoy.
Matt