My thought for the 2 cents its worth. We are in South Eastern Ontario as well and have driven it several times. Not recently, it's been years. It is a 24/26 hour drive. In Feb, driving through Pennsylvania could be terrible. If there is an sort of winter storm at all you can forget about it, your going to have to hole up somewhere. Those hwy's can be treacherous in the summer months, in the winter they can be even worse. One summer a few years back on our way to Myrtle Beach, there was an accident that had us sit on the hwy not moving for 6 hours. We had friends who had to find a hotel and couldn't get out for days due to a blizzard one year. Now, this isn't an everyday occurrence but keep in mind your passing through mountains and that's even trickier. I'm making this sound horrid but it can be.....or it can be amazing. My point is you just can't tell.
I like to board a plane in the morning and be their for lunch. It's only two and a half hours and your done. Quick and easy. I understand your fears though so it's something you have to decide if your comfortable with. My comfort level, for all the reasons I listed above, would be with flying.