Always works ... and free!
Because (fresh) sliced bread is the biggest thing since Gmail. And because Toronto's equivalent to Montreal smoked meat, back bacon on a bun, doesn't get enough respect. (Also worthy of getting crumbs in your keyboard: Eggplant parmesiana, free samples at Alex Farm's cheese.) Yum.
It's Sneaky Dee's! 'Nuff said.
If I had a dog, I would take him to Dufferin Grove Park and let him off his leash. Then he would be free to play with other dogs and I would be free to play with other humans... or humans pretending to be level 36 elf mages, if I brought my laptop. (Truth? I've never played an online RPG in my life. But at least elves don't pee on you or expect you to play this thing called 'catch', which is -- c'mon -- the stupidest game in the world.) Other outdoor venues: Yonge-Dundas Square and Harbourfront.
Despite the name's disturbing implication that you might get home, unwrap your bedsheets and discover a tiny, helpless human being inside, the free-wifi-while-you-wait-for-your-laundry concept is genius. Bonus: Free coffee, open 24 hours.
Okay, so I've never actually been here. But for people who actually get pedicures, what could be more geekishly self-indulgent than having your nails done while you gossip over Facebook? (Answer: Nothing, you net addict.)
There are about a million places on Queen W that offer coffee and wifi, but Tequila Bookworm is especially cozy, totally relaxed, and I hear they have good soup. (See: other favers.) Bonus: If you're there from 4-6, you get to watch the clientelle flip -- out go the bookish coffee drinkers, and in come the after-work hipster beer drinkers.
The Danforth is a barren wasteland when it comes to wifi. You have two options: Try the Carrot Common (Timothy's only sometimes works for me), or, if you like to drink and surf (and based on the growing number of bars in the city that offer wifi, you do), you can grab a seat at the Court Jester. It's busy enough to provide lightly distracting human theatre, but not so busy you're worried about someone spilling a beer on your notebook. Bonus: Random West-indian offerings on the menu.
I don't know how condusive Woody's is to working, but it's big enough that you can probably set up at a table tucked away under a staircase somewhere. (Maybe. If it's not the weekend.) Bonus: Guaranteed to be the only place in town where there's more porn on the TVs than there is on your laptop.
At once crunchy (greener disposible cups; organic coffee) and techie (more extension cords for your laptop than you can shake a joystick at), I once overheard a conversation here about running Linux on a cash register. If that's not your bag, someone described Linux Caffee to me as having the 'most beautiful nerds in the city.' Bonus: Music and coding events liven things up.