I've gotten several found cars stuck on rocks and barriers, but since I've upgraded my vehicles I've always been able to get out of those situations. upgraded cars seem to have much better off road capability in general, I have even taken shortcuts off road or thrown the car down rocky cliffs and been able to flip the car at the bottom. It also changes their storage, my muscle car went down to just 2 slots while my ambulance increased to 8.
You can find upgrades with traders, they cost a couple 100 influence, I don't know if you need a skill to use them.
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