Brian, it's probably correct to say that if you stripped out all the extras that you have put into your boat over the standard spec, you would have a really tough time getting back anywhere near what you paid. It is those gazillion dollars that makes your boat a desirable used purchase.I haven't lost anywhere near that on my boat. Wow! Why dd he take such a hit? If I sold my boat right now, I would not make money, but I would not be out much from what I paid new either. That does not include the gazillion dollars I have thrown out at it since I bought it, which you will never get back, but that is not a bad return for the years of use I have had.
My ex boss (very wealthy) bought a Bene 50 in 2008, brand new, on a whim, never owned a boat before. He filled it with stuff to the tune of NZ$130K. Within the first year of ownership, he decided that sailing was not his thing and he bought a high-end power launch. When he came to sell the Bene, he asked the original purchase price of just the boat and after 18 months of trying to sell it he eventually off-loaded it at NZ$80k less than he paid for it not counting the toys. The boat was seldom used, effectively in as -new condition. So he effectively lost NZ$210K within a couple of years.
We have friends that bought a Bene 40 two years ago brand new. They paid NZ$325k including taxes. They have spent another NZ$100k on it since then and counting. If they sold it tomorrow, they would possibly get back most of the $325k but the rest would be school fees. Consequently, it is probably true to say that the boat has devalued by 30% in two years.
So IMHO, the notion that an "ordinary" boat retains value is smoke and mirrors. Maybe Hinkley's and similar boats do but the average production boat? I don't believe so.
I have no illusions about this, when I come to sell my boat and am able to recover 50% of what I spent in total, I will be happy. There is a cost of use to everything in life that is hard to avoid.