I am very familiar with both of those spots on Pennsyltuckian. The first pic proved a challenge for both wagons in our group, an 80 and a 62.
That second one was also a tough for my 40 and the 62. They seemed like the most benign spots on the trail until we got on them.
Given that these were probably the hardest trails I have ever wheeled, rock and hill-wise, they weren't impossibly difficult (in retrospect... at the time I was sh**ing myself).
I gauge difficulty by how much I have to deal with body damage and mechanical breakage, and getting stuck to the point of needing a winch. I had to pull cable just once and I got out without any damage or breakage. (Thankfully I didn't have to worry about too many trees on these trails.) I wouldn't have even attempted Insanity and KGB without the encouragement and spotting from Cam. Pennsyltucky wasn't as intimidating overall but did have more trees, we ran that on Friday. We took it VERY slowly with the big wagons - that made these trails "easier" in that we could take our time picking lines and crawling... good for our success, bad for those waiting for us to finish (sorry folks)
I have an H55f 5 speed to a Marlin 4.7 ToyBox to a split case to 4.56 diffs (something like 235:1) all behind a 2F... with ARB lockers front and rear.... that combined with Swampers give me a fair bit of advantage.
Pics from OB... LOT of pics (unedited)... first of Pennsyltuckian then day 2 with Cam and friends on KGB and Insanity. I'm in the grey 60, Jon is in the black Lexus, Brandon is in the green 40, Karol is in the yellow FJC and you know most of the rest of the guys from the 2nd day...