Wes,
My rear driveway is much like you describe. When I back my TT into position, the TT is almost level, while the TV is pointed downhill. Not only that, but the TV is off camber compared to the TT. So much so, that when I take the tension off the screw jacks, one side is backed off almost all the way, while the other side is only part of the way. When I pull out with the stinger, the hitch head is at a pretty sever angle. Not only that, but the hitch head is physically shifted off to one side since I was backing up when I stopped.
I have no such difficulties getting hooked back up. To get the stinger back in, the truck pretty much has to be in the same position. It gets there by simply making sure that once I'm engaging the hitch head, the steering wheel HAS to be straight. I have found sometimes that when I thought I was in position, I wasn't. That has been the times it has caused me issues. Not going straight back toward the trailer will get you everytime, as the head then starts pivoting, which changes side to side angle.
Of course, as with all things on this site, things vary between setups and such. And as far as short trips with the EZ lift, that certainly does makes things more simple for those.
To the OP, good luck with the PP, as you will come to love it more and more with that big rig of yours.