Depends on width of trailer, I know i've seen them at least 9' wide. Why not unbolt sprockets so track can spin free making it very easy to winch on? As long as the trailer won't break and track chain is comfortably on the trailer I wouldn't worry about it. You're only moving it once, you can make sure it's perfect and tie it down extremely overkill so it's not moving. Again with the height could easily just drive your path ahead of time to get out any potential height issues. When I was younger and not as bright I was hauling a Deere 225 on a 8'6" step deck and had no issues breaking the trailer, and with thumb etc it weighed 25 tons. And it stayed shiny side up except for one very close call