I used to have two 955K traxcavators. One had the factory cab with ROPS. The other had an open forestry type ROPS. I pulled them behind my Mack with a 300 plus engine on a Linden tilt bed pintle hitch trailer. The trailer had air brakes. It only took a minute or two to load or unload; the tilt bed trailer made it simple. Being a crawler, the loader was solid on the trailer and never moved. I did throw a chain and load binder on each side, tied to the track front and back and through tie down loops on the side of the trailer.
Over height was not a problem since the trailer had smaller wheels (less height) than most highway trailers. But check your total height to make sure.
If I remember correctly, the 955s weigh a little over 15 tons. So a 20 ton trailer should work well.