I am currently struggling with this now also. We have a 4025 mahindra, fel and brush hog. Our current 16' trailer with 2500# axles, no brakes will not work.
I have been scouring Craigslist and trailer shops for the best deal on a 20' with brakes. I found a really good deal on a pintle hitch with 12000# axles. My dad said it would be too much trailer, for what we have to haul.
We drive safe hauling loads, but I guess I just worry about going down the hiway on a rainy day, and some idiot cuts me off.