[1] http://www.pm.gc.ca/eng/news/2016/06/28/canada-lift-visa-req...
I like it here, and I'm happy with what I make, but when you factor in the exchange rate, a typical US developer would take a huge salary haircut working here; probably 40-50%.
You're spot on w.r.t. most living expenses, too. I've got a big apartment in a part of Toronto that I really like for $1200 a month. Buying a house in this city is another story, though. On my grandfather's street, smallish 3 bedroom detached homes are selling for $1.5 million+.
Are you seriously comparing SF living to Waterloo living? There's a reason it's 1/4 the price. It's a running joke between every single undergraduate student with significant experience in SF that we want to get out of Waterloo.
LRT opening up? That's a joke. How exactly is the LRT going to help the startup scene?
You show up at the border with your passport, the fee, and few documents from your employer. They do some stuff on the computer and then awkwardly disappear for a few minutes. You pay the cashier and the guard reappears with your completed work permit. Done.
As far as I know, there's also not much paperwork for returning to the US, though you're supposed to inventory all of the stuff you bring back with you.