I did not think there were roads 7 hrs north of TBay,

Are you from Red lake?
Must be a mining towning
Yessir, in fact, I think the most northernly highway in Ontario, Highway 105, terminates in our town center at the only stop lights in town (and, HERE'S a big tourist grab, the Most Northernly Stoplights in Canada!). Big time mining town--Goldcorp Red Lake Mine is the jewel in their crown and they are one of the biggest mining companies in the world. Recently, there was also a Placer Dome mine (Barrick Gold) but Goldcorp took over Barrick so it's all one mine. Mine shafts are like trees up here (Well, the millions of trees are REALLY like trees, but you get the idea).
1) How likley is this to be a problem on a 2001 truck? What could possible cause a truck so 'young' to not pass?Very unlikely it would not pass.
2) My 'permanent' address is in northern ontario, at my parents place, as I'm still a Student. So, odds are I'll be registering it up there too--And, up there, we aren't required to E-test our vehicles. Is this an easy out? It seems TOO easy, so
I feel like maybe I'm doing something wrong! 
I'm 100 miles north of Toronto and we don't E-test plus my Porsche is a no cat car. Save your guilt for something really questionable.

Good enough for me

Northern Registration it is!
Like buying anything from Steve's carlot would be questionable indeed. A 2001 GM truck should be fine as they are a well built unit as long as its bought anywhere else but there.

Good to know, thanks

And the good news:
I got the report back from the garage, and the truck needs new rear brake pads & rotors and a new tail light bulb to pass safety, which isn't too surprising given the mileage.
I've spoken with the gent in charge, and we've discussed this work, and his $9800 asking price has been negotiated down to $9100.
I'm transferring the money and he's mailing me the registration. I've bought myself a new truck!
Thanks a million for all the help on this guys, I Couldn't have done it without you!
Cheers and Thanks!
Craig