Posted: Mon Jun 30, 2008 8:38 am-
I applied for my TN about 4 weeks ahead of our actual border crossing (we wer moving from Sudbury ON to Nevada), mainly I wanted to make sure I had no problems at the border on the actual trip down. The border guard I got was great, he had not problems with my application (everything was in order, all the pages were in their own plastic page holders in a binder), we crossed in Sault Ste. Marie, (not the most convenient for you). He actually post dated my status until we planned to move (about 4 weeks later). When we crossed again I had to apply for TD status for my wife and son, the guard that time gave me a little bit of a hard time, but not too bad, he also said that the original guard should not have post dated my status. SO.you can actually apply at any time, but it may be effective on the day you apply, so if you apply a month early you may only get 11 months out of your first application, or the guard might post date it for you (I wouldn't expect it but it might happen).
To answer number 2, you can go to the border, get your TN status and go back to Toronto, that is what I did, when I returned to Canadian customs, they asked how long I was in the US, I said about a half an hour. I spent more time driving to the border than I did getting my status. Hope this helps!