So, you believe your boat was worth over $280K three years ago ?

I've bought three boats, and sold two in the last 15 years.
My take on the sailboat market, in that time, is that well maintained boats 10-30 years old were basically maintaining their original selling price.
30 years old seems to me to be a magic number in a boats life to many people i.e. they wouldn't consider any boat over that age (I don't really get that).
Then three (or a little more) years ago there was a sudden decline of at least 33%, possibly more.
Luckily, I sold my last boat at the end of 2007 for a little over what I had paid. Unfortunately I spent three years looking for the perfect buyer, who would appreciate all the work/upgrades that had gone into the boat and be willing to pay for them. During those three years I spent thousands on maintenance, storage, and advertizing. My cost to sail the boat during those three years was around $10,000/hour of sailing.

My prediction is for a continued decline in used boat prices, for all the reasons others have already given.

Cheers,
JM.