My all-time favorite approach is to travel with other Hummers and let a couple of them go first!!!
Not only can you see the lines and realize what your in for....but once a couple of them go...then you know, being that you've got the same vehicle, that you too can make it.
As for doing scary stuff while on your own: not advisable!!!!
I've been to a practice track and played with taking sideslopes that scare ya. I've also been up some pretty steep hills and after doing all this I returned to a nearby hill where there is a trail that runs straight up the front. I never really messed with that trail....but after all the practice and stuff...that hill looked pretty mellow and I went right up it!
In other words.....practice and you know you can do, and don't exceed that while traversing new and unknown obstacles.
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