I would consider using public transportation from NYC to Boston and back, and also from Boston to Salem and back. The NYC and Boston metros and in between are not pleasurable places to drive.

Donna, US-287 between Dallas and Amarillo is near-freeway quality, you can make good time on it. 650 miles is indeed a long haul but it's not that terrible. You will want to make a very early start to get out of the DFW metro before the height of morning rush.

I would purchase a Rand McNally road atlas for planning, there is no substitute for paper maps.