I’ve had my eyes out for a decent 5x8 or 5x10 enclosed trailer for quiet a while now and everyone wants top dollar for them. Trailers do seem to hold their value very well.
Yes used trailers do list for quite a bit more than a reasonable person thinks they might be worth. I also find they don't sell. It seems the way to go is to buy new, then risk an abused trailer with a bent axle that has been cleaned up nice.
My co-worker had is lightly used 8x20 enclosed car hauler for sale at $5,000 for six months. I bought it months later for $3,000- and felt I overpaid at 3k, but I knew he only used it a handful of times.
I also tried to sell my steel plated carhauler for $2900 (I paid $4200 new). I took it off the market after 30 days.
Lesson learned- people say used trailers hold their value- my observation is they rarely sell.... just check used trailers at auction on ebay that actually sell.... very few meet the reserve.