Welcome to RTA!
You didn't say where in NJ, or in WV, so I took Paterson and Charleston, respectively, to do some rough calculations. You're talking about a 2500 mile trip. If you took 500 mile days, it would take you five days driving each direction, which leaves you 4 to 6 days to look around at the GC, stop and sightsee along the way.
As for Alaska (another trip, I know), my best advice would be to wait until spring of the year you want to go, and get the latest MILEPOST book. It is the best set of information you can get, regarding the Alaska Highway ("Al-Can"), and the highways that connect to it, and how to plan for it. And if you don't already have passports, you can get those applications underway, as you need them now to get from Canada back into the US.
Donna