Any chance of leaving the implements behind? (Loader and brush hog)?
I'm seeing some potential problems with both of those attached. The main thing is your total length. With that load, you're going to want at least 500# of tongue weight and personally, I'd probably go closer to a half-ton. To get that tongue weight, you're going to have to drive the tractor/implements on then stop once you get to the desired weight. Once you go over about 300# of tongue weight, you're now guessing based on how much the truck is squatting. Wherever that point is where you stopped the tractor is what you have to live with. Due to the length of the tractor/loader and brush hog, you may be sticking 5' off the back of your trailer. Not good so then you have to look at bigger trailers (cha-ching $). It may be cheaper to just get another brush hog and leave it at your destination.
I'd suggest you go to some trailer places and explain what you need to do. Take measurements and weights. They should look at your brake controller, hitch, tranny gearing, tranny cooling and dimensions/weight of your load and come up with some recommendations.