Minnesail, thanks for pulling that together. It's a nice contribution of actual data to the discussion.This is a chart of the asking price for a Catalina 30 from 1975 to 1995. I don't really see a sweet spot, it looks like pretty linear depreciation to me.
I looked around for other boats with a large number of listings. The Catalina 36 has 49 listings. The trendline is pretty close to linear, though the datapoints are mostly in a small cluster. I'll see if I can find other examples.
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