Trailers with long overhangs will always have this problem. I prefer a skid plate over a roller. Any kind of roller will hang down and be a catch point. Also, you can lose some of that precious ground clearance by hanging a roller lower than needed. A roller recessed in a skid plate would be ideal, but let's not get carried away.

I would suggest going to a welding/fab shop. Have them extend the frame rails if necessary and add heavy skid plates. The idea is that the skid plate will make contact first and nothing "soft" or "catchy" (like stabilizers) hangs below the line from the rear tire to the skid plate. When you approach the steep spot, the skid plate will make a smooth engagement with the ground and lift the rear of the trailer slightly until you are clear.

Yes, it makes a terrible noise and yes, you are dragging your trailer through the hump or trough. But if the plate is tough, there will be no damage... much better than the carnage of ripping of all the important stuff back there.