First watch the classic movie,
The Long, Long Trailer (1953)!
It just snowed today across the Tioga Pass, so make sure to take chains.
It's nowhere near as scary as it was in the 1953 movie, (just don't take any rocks)!
I have made the trip several times pulling a PopUp with an SUV, and in 35', 40', and 42' motorhomes, all pulling a toad. A 5th wheel shouldn't be a problem, depending on the torque in your TV.