I totally agree that most Owners of well maintained boats typically take a haircut when selling, but that's kind of the nature of the beast.
I just cringe when I hear people state that they are going to "Invest" in a boat!

Folks, the vast majority of boats out there are not "Investments", in accounting parlance, they are "Depreciating Assets", in other words, they will go down in value no matter what you do (when you eliminate things like Covid pricing).
We didn't get any of the boats we've owned with any expectations that we would make money on them when we sold them, although we've always sold them for more $$ than we purchased them for . . . BUT the purchase price is only the initial ante, making them YOUR boat adds many, MANY $$$ to the pot than just the initial purchase price . . .
That said, with every boat we've owned, we, personally have been made richer by the many wide and varied experiences, and the beautiful places


we've traveled than the amount of $$ we spent on those boats.
Our current boat, over the past 4 1/2 years, has taken us from Seattle, WA, to Glacier Bay, AK, to LaBelle, Florida, and many many places in between. We never in our wildest dreams expect to get out of her what we've spent on her, but the next owner will get a boat that is ready to cross Oceans. . . . for a fraction of the cost that we've spent on her . . . .