Welcome to the RTA Forum!

I'm a little confused, is this trip so that you can move to Pittsburgh? You mention moving in your title, but then you say you don't yet know where you'll be starting from, and it seems strange that you don't know where you currently live.

You also say that you are "youths." What does that mean/how old are you? If you are under 21, renting a car would be virtually impossible, but if you don't have a car, I'm not sure what your other options would be.

In terms of winter driving, many, if not most, days out of the year, you'll see perfectly fine conditions, but you do certainly have to be prepared for a winter storm. The best thing you can do in that situation is to be flexible and if you get involved in a storm, pull off and wait for conditions to improve. It is rare when a storm significantly impacts the interstates for more than a day.

We can't tell you routes, since we don't know where you're starting from, much less if this is a trip to explore or just to get from point a to point b as quick as possible, but when building your plan, you should limit yourself to about 550 miles in a day, and that's if you aren't planning any significant exploration.