We had a steep driveway and entrance to the road in front of our previous house. Once I removed the sand pads from the stabilizers and learned to hit that transition from the road to my driveway at an angle instead of straight on, it was fine. I would have to put a fair amount of blocks under the tongue jack in order to get it close to level. Obviously, both wheels had chocks and I remove the wheel from the tongue jack.
Also in our neighborhood, someone had a full sized TT that they did the same thing to but because the TT was so long, they had to build quite a tower of 4"x4" blocks under the tongue jack and front stabilizers. The TT had a higher ground clearance than my PUP so I don't know that they had to angle into the driveway or not.