We used our Southwest card for most things in Vancouver because it doesn't have a foreign transaction fee. I was concerned about the whole chip and PIN business because I don't have a PIN. Before leaving, we called and I set up a PIN, but later discovered that's a PIN if you want to get money from the ATM, not for transactions. Since you don't have a PIN here, you won't use one there. It's no big deal.
In terms of cash, you won't need much. We really only used cash a couple of times. The only time we really needed it was at the airport when trying to take the Sky Train, for some reason the ticket machine wasn't accepting our credit card. We used some cash there. I recommend just grabbing some out of an ATM when you get there with your bank card. You will get charged a fee, but it will be less than the hit you'll take if you use any of the money changers there.