I don't really see anything that's substantially changed in your basic plan in getting to NYC, so I don't see what would really change in terms of the Advice.
As long as you see good weather, this is a trip you can make in 2 long days. Once again, Toledo is probably your best bet for finding a variety of rooms, but you really should not try to push farther than that (including trying to go to Cleveland in one shot.)
The biggest problem is you are traveling in winter, and lake effect snow could become a problem, and that could force you into adding a second night on the road.