I find towing off-road is fun. It's amazing where we can take trailers these days! I think a big part of successful towing off-road is knowing where you can and cannot take a trailer.
-Plan your routes.
-Avoid tight switchbacks, and narrow trails where others have to pass.
-If you have concerns, get out and walk ahead to see if you can get through.
-Keep an eye out for wide spots to turn around, or back into.
-Practic turning around in as short an area as possible.
-Practic unhooking the trailer and turning it around if the worst happens.
-Be okay with parking the trailer at a campground and go expore with out it.
-Plan a recovery if you had to unhook and retreave the trailer if you got stuck (like if you had to winch the trailer out of mud/sand).
I've had to do turn arounds on trails. One time, I could not back up a hill I had just driven down and couldn't go forward, so I unhooked, pushed the trailer into a bit of a ditch, turned my Jeep around, and then rehooked up. Another time, I had to drive my Jeep up onto a berm on the side of a trail in order to get the trailer straright, so I could back the trailer up straight enough to get my Jeep turned around. That's all fun!
I'd also say that off-road you've got more to hit the trailer on when making turns, so rememeber to make those wide turns so the trailer doesn't get hung up on a tree or rock on the side. And last, keep weight in the trailer low. IMHO, I see some trailers with too much weight up top and just look tippy to me.
Enjoy the teardrop!