Steve,
I agree. The front hitch would be a nice addition for a long reversal of direction on a narrow path. The jack wheel might be useful in some cases to turn the trailer around in it's own length too. We went about 7 miles up a very narrow path where it was not possible to turn around and all the way up I was hoping for a spot to turn around or an intersection. Finally found a wide spot at the top.
Sand is another concern out in Death Valley. A spot we go has about 6 miles of flat sand to cross to get to our spot. I'm not against airing down the trailer and the truck and keeping the momentum up. I'm not going to install a winch, but a winch and a Fortress anchor could be handy there. I always shave a compressor on-board.
Another good piece of recovery gear is a heavy duty brush guard front bumper, like the one on your truck, to help "recover" from a deer collision that could easily disable an unprotected truck. Forget about getting stuck in the mud, a bashed in radiator, in the middle of the night, way out on a lonely road, is not fun.
I just can't plan and prepare for every imaginable problem. Pretty soon we would have so much gear we couldn't go, and I could still imagine more potential problems to prepare for. Much better to be prudent about what we venture into, than planning on getting stuck and bringing all the gear needed to get out. Even stranger is expecting Oliver to tell us how to get out. An impossible question for them to answer.