That's not an easy question to answer. First, what are you pulling it with? Bumper pull or gooseneck? I expect your tractor and implements could easily exceed 7000 lbs so weight is a big factor. With the FEL, and a bushhog attached, the length will be more than you think. Measure it first, then add some.
The very best is a gooseneck deck over, with a 20 foot deck and a 5 foot dovetail, with flip up ramps. With two 7000 axles. That will do anything you need. Personally, I would definitely get a deck over. And simple flip up ramps. And if possible, a gooseneck. To me any bumper pull that will haul a 40 horse, with a FEL, loaded tires, a rotary cutter, will be at its limit. It goes back to doing your homework. The length, weight, maximum width (of the widest implement you could ever foresee having), and the rating of both the trailer and your truck all need to be accounted for.
My tractor with a grapple and rotary cutter is long! I have to pull forward with my FEL up to allow the ramps to fold back up flat. But then I can back up to center the weight and get my FEL down flat. It's not a problem
But a trailer is rarely too long, but often too short!
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