Having both bought and sold a boat within the last year I think that boat prices are way down. It is a buyers market. So, older boats that may need some work are being sold very, very cheap. Newer boats in good condition are being sold for much less than a few years ago and way less than their owners think they are worth.
You are right on target. We sold/bought last year and are on our third boat in as many years. We were trading up until we bought something that was in the size we wanted. I've been watching the market like a hawk over the past four years, and continue to watch it in the event that we decide to trade up again.
It is a total buyer's market. I've seen 40'-50' Formosas going for close to half what they were priced at a few years ago. Irwins that were in the $50,000 range priced at $22,500. Many more examples. Then you have the boats that are in need of a repair that an owner would have gladly done five years ago so that he could have gotten full price, but he can't afford the slip fees, let alone the repairs, so you have a beautiful boat that has a bad engine, or has something else wrong going for a song. And yes, a lot of free boats are out there.
As the market softened three years or so back, I watched as the smaller boats fall off their price points. You'd see the 20'-26' boats being sold cheap. Then the 28'-34' boats started to soften. Now you're seeing really nice boats in the 35'-45' range drop drastically, and the boats in the 45'-55' range are also really softening.
Now is a great time to buy, but a terrible time to sell. In the position you are in, you could take your time and end up with a great boat at probably 50% of what you would have paid for it three years ago. Good luck to you!