In my experience used mower pricing just isn't that cut and dried. Location seems to matter a lot and I'm not sure why or how that works. Ric, you might be able to buy that mower & trailer for 2000 all day in Florida but I don't think I could find a deal like that here. If I did I'd have to look long & hard. If I bought that for 3000 I could sell it here at a decent profit.
I can drive 2 or 3 hours north or south and find some sweet deals but resale prices vary a lot according to where you are and locally prices tend to be quite a bit higher. A 6x10 trailer like that would be 1100 to 1300 here and it wouldn't be as well made as that one. Used in that condition would be 800 to 1000. Hell, even that toolbox would be 100 to 200 here.
That is one reason I don't usually ask about used equipment pricing.