Trailer value

I bought one a few years ago just like you are describing that had a winch and needed the floor replaced for $1100..

Just like everything else, wouldn't the location, location, location of the item impact it's value?

I'd take it over to my local "trailer store" and ask them to give me both a trade-in value and and private sale value.

Obviously the condition is going to weigh into the value big time, especially if it needs to be inspected (brakes, lights, tires) and will or will not pass as is.

Look on/search CL

Different cities will have them in different classes.

Depending on condition I've seen simlar go between $500 and $1500.

check harbor freight they sell trailers cheap and will limit somewhat yours top price

It's likely a breakaway brake. A requirement in many states now.

Your 16' trailer if for sale here would be $1,000 give or take with a usable deck in driving condition. Paint, fresh tires, good deck, bulldog hitch, tongue jack, and weight, spacing, and size of steel undercarriage all can raise the price.

I don't know what size backhoe you are thinking about, but none that I know will work with a 16' trailer. A full size hoe is crowding 27' and

Back hoe trailers are usually 3 axle or 2 axle with duals. Better check the GVW of your truck, I suspect your way past a 1 ton.

Most likely a safety disconnect brake actuator.