Redrocket,
I did this weekly from mid december until mid to late march. I've been stuck at the top of snoqualmie pass for 72 hrs because the pass was closed, could not even ski as it snowed over 6' at 25f. very wet snow. In the midwest it is at least dry.
Wet snow is harder to drive on than dry snow.
I've seen mid westerners come out here, say we do not know what driving in snow is.....they end up in the ditch.
Yes snow is tough to drive in, was I worried ea weekend, with 4 kids in the truck. sure. but at the same time, if I had listened to some saying no don't go because I might have to drive in the snow.....i'd never have teh 200 some odd weekends with my kids as I did.
I bought my trailer with its intent to use as a ski hut. it did not get used but 1/4 of the time from april to december vs the december to march time. Come to think of it, I drove home from Schweitzer the first or 2nd weekend in april one year with it snowing from just west of spokane all the way to denny creek west of snoqualmie. With 6 of us in a crw cab pickup! Should have chained up at the pass, but did not. 6" of slush on the down hill. 200+ mils in 2wd towing with snow.
I've had some interesting times towing, seen some iteresting things. but I will not discourage folks from going. To me, if we know if usses towing in these conditions, say what they are, how to avoid per say as in once there, this is what you do. Hope the person can say, I seem to be here, X said do this. so I'll try it.
I'd do the trip the OP wants to do in a heart beat. even with a rwd truck! I'd do it with my 2000 rwd reg cab truck. Towed with my dumptruck with a detroit locker in the rear on snow up and down some 10-20% grades. No 4wd mind you! chains yes.......go slow ad steady.
marty