Car is in Canada safe and sound. I had a friend pick it up for me because I've been overseas. Here's what I discovered from this adventure:
-No duties on cars over 25 years old
-Even though we have the HST they still split up the taxes (5% crossing border and 8% when you register the car in Ontario)
-The car had to be registered in friend's name when in Canada because he's the one who brought it here. To get around this you'd need a notarized letter stating that your friend is driving the car and your name will be on the new title. This isn't an issue for me.
-The MTO doesn't give out "trip permits" like they used to. They'll only do a temp plate with the original title in hand.
-You can get a temp plate in Pennsylvania and drive all the way back home with no issues at the CDN side of the border (this probably doesn't happen all the time). This is a grey area and it may or may not be a problem.
Thanks for the thread and all the help!