I have done well with all of my TTs.
My first was a used 78 Prowler. Paid 2300, used it about 4-5 years and sold it for 3200.
Bought a new 2001 Wilderness in 2000 for 15500 out the door. I had seen this unit for 25-28K all over town until one dealer want to sell his bad.
I sold it in 2010 for 9500. Asking prices for used ones nationwide were 15K. It was sold in 15 minutes with backup offers.
My current TT was bought far below MSRP, so I expect to well on it when the time comes.
I always pay cash and always sell my old units, afterwards.