I've got several miles with my travel trailer and 1/2 ton Tundra with bags and a WD hitch....it's no problem at all. That said, not sure the WD hitch in the winter is the right setup. It really depends if you're talking about high-speed interstate stuff, or twisty mountain roads. As Matte said...getting the whole truck/trailer situation level is the key to good handling. Bags let you do that.
Haha of course you have a Tundra, that's all everyone drives in Nelson.