Interesting discussion.
Another point which has made an impression on me is the size of boats these days. In our cruising ground Cuttyhunk is a stop for just about every boat headed to the Vineyard or Nantucket. Back when I sailed a Pearson 30 (early 1980's) a 35 ft boat was a big boat. Now when we go to Cuttyhunk you rarely see anything 35 ft or less. Most of the boats are 40+. So where are all the Catalina/Pearson/Tartan/Sabre 30/32's? How (if at all) does that data point fit in? I know those boats are still around since there are 2 P-30's and a couple Tartan 34's in my marina. But I never see them on the water. Btw, I don't think the absence is a good thing. I'd like to see more young families in their 32/34 ft sailboat in these harbors. Back in the day we knew families with boats as small as 27 ft who would be on the water. It seems these days we are surrounded by geezers like myself in these anchorages.
Btw, I know powerboats are popular these days but you can't sell a SeaRay or like model on the market. It is flooded with used ones.