I have been doing the same thing since about your age.Talk to your co-workers who do it and the ones that have done it for years.They know from experience what works and doesn't.Unless you have done it you don't have a clue as each trailer is unique as to how it handles the cold.They will all freeze at some point.
As to traveling in the snow and ice,have chains and or studded tires when applicable for the trailer and truck.Ignore the 1/2 ton jokes on power..An engine is an engine and power has nothing to do with the GVWR of any tow vehicle.
Staying in a RV is much much better than a motel and it's yours,a home away from home!If the cost was the same,I would never stay in a motel while off working.It's just not the same.