T-Mobile is more convenience if you got down often enough, so the $100 cons is not relevant. Setup google voice while you are in US to call back Canada for free, or use the free dell voice. So there is no cons.
I got a sim and shared it between friends, and we already used up $70 after 4 months.
You don't need to prepare anything, just go across the border and put in the card.
4g is quite fast when available in urban area, 2g is good enough for google map gps.