Morning Allan, Other guys are right, don't buy too big. I had a 36 foot triple axle that I got for a song, couldn't really use it. Damn thing was huge, scrubbed tires like you wouldn't believe (tandem duals are much better than triple singles) and you couldn't use the whole deck unless you were hauling straw or something light. Also, go dove tail, either pop-up or flip over ramps. Problem I have with flip over ramps is you have to move the tractor/load forward enough to flip the ramps, could see situations where it wasn't possible. I had one guy pick up a tractor with a hydraulic pop-up dovetail trailer, and that was a nice looking set up. Oil bath bearings are nice, almost zero maintenance, but running around local, just pop the caps on a greased bearing once in a while and you will be fine. If you go used, look close at the straightness and the deck. People tend to load to volume rather than weight on those trailers, easy to overload a trailer with round bales. Deck wood is expensive...don't buy one with a bad deck unless you price the wood first and the cost of the trailer is in line... I agree on the winch, you will use it and love it if it's there, cuss how to load things if it's not. Add a couple snatch blocks while you are buying, useful to change the direction of pull to "straighten out" a tractor. Like was said below, you will want a bigger one at some point. When that happens, buy a 2.5 ton cab/chassis (or your grain truck), put a ball on it and use it, pickups today have all the power to pull anything, but people forget you need stopping power more than go power.
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