A photo of just the driveway won't look too bad. I would need one of of the trailer backing in, which I don't have.
The problem is that one side of the trailer goes over the curb and the other side goes in the dip between the road and the driveway. The TV is at the crown of of the road. This causes things to be at a strange angle. I can't disco or loosen the WD hitch either - it will hit the driveway when backing in if I do that. Many times when backing up, I have to put my foot in the throttle way more than I should have to. I'm pretty sure that if I can get rid of the dip so that I'm backing on more level ground that I can eliminate whatever is binding before something breaks.
I suspect that I need to fill in about 6" at the point where the driveway and street meet.
Another approach would be a variation on this:
![](http://www.instructables.com/image/FW5MTYXOKIEVYDYYJ0/The-curb-ramp.jpg)