Funky driveway = towing concern. Looking for some advice.

Judging from your pics I'd be more concerned about backing up that narrow drive and would instead want to pull it in and pull it out. That of course means having the space to spin the trailer around once in place but that surely would be easier than backing up that narrow drive. The dip I don't see as an issue as you'd sometimes run into this in campgrounds but of course the pics don't show that particularly well.