From Toledo, it looks like Nubs Nob/Boyne Highlands (MI), Holiday Valley (NY), and Seven Springs (PA) are all in the 4:30 - 5:00 hour range.
My personal opinion would be to do trips to both Holiday Valley and Seven Springs and see which you like better. Seven Springs would have the advantage if you like a lot of park. Holiday Valley if you like exploring different areas. (There's also Holimont next to HV, but it's a private club and open to the public only on non-holiday weekdays.)
So I say Holiday Valley or Seven Springs over any of the MI resorts. (Unless, maybe you're talking real late season when the MI places might still be open and the others not.) Driving from Toledo to Holiday Valley, keep in mind that from Cleveland to NY, you're in the prime zone for lake-effect snow.
(I actually don't like HV very much, for some completely irrational reasons, but I find myself recommending the place to other people. If I'm going to western NY, I usually go to Bristol Mountain instead. (Bristol doesn't have much lodging within 20 minutes, and there's no nightlife unless you head into Rochester or suburbs. For me, these aren't big minuses. For others, they could be deal-breakers.))
Sooner or later your legs give way, you hit the ground.
Last edited by MikeIn248; 10-21-2013 at 01:26 PM.