I'm working in Toronto at the moment and am back and forth all the time. I tried getting VS to quote me a fare, connecting in NYC/BOS/etc - but they were incredibly uninterested in doing so - claimed it would take them two days to confirm seats on connections from JFK or EWR up to YYZ. I didn't want to take the risk of booking a separate connecting flight in case I missed it due to a late inbound - I wanted reprotecting onto another flight ... and ended up giving up on VS and am flying on the dark side. Oh well - BAEC Silver, here I come... VS FC Red, here I come too

One other observation is that the flights between NYC and YYZ are expensive... in the region of 300 - especially when you consider the actual distance flown. Porter are good, and cheaper (~CAD$300), and do fly from EWR to Toronto downtown airport, which avoids the mess that is Pearson airport, but they're not necessarily the most reliable of airlines (ad hoc cancellations all over the place), and they fly those planes with funny little whirly things on the wings. I like jet engines, for some reason. :/