Transfers and Toronto

Hi all,
You're always so helpful with any questions I've had, so I hope you won't mind a few more.
Pondering an October holiday in Toronto and NYC. Can't decide whether to fly out to BOS or NYC, then get a flight to Toronto. Surprised how much the flight would cost too, any low cost carriers that don't appear on Travelocity? NYC has a small advantage at the moment as I could get a 747, which I think is better as I may upgrade with miles to Upper Class on the way out. Is there any reason I should fly via BOS though?
How long should I leave for transfers at the airport? If I did take VS003 and land at 16:40, what's the earliest I should book my flight to Toronto for?
VH's selection of Toronto hotels is also a bit poor, but as I can get 10% off, maybe I'll just go for one of those anyway.
Thanks for any tips!
Mike.
You're always so helpful with any questions I've had, so I hope you won't mind a few more.
Pondering an October holiday in Toronto and NYC. Can't decide whether to fly out to BOS or NYC, then get a flight to Toronto. Surprised how much the flight would cost too, any low cost carriers that don't appear on Travelocity? NYC has a small advantage at the moment as I could get a 747, which I think is better as I may upgrade with miles to Upper Class on the way out. Is there any reason I should fly via BOS though?
How long should I leave for transfers at the airport? If I did take VS003 and land at 16:40, what's the earliest I should book my flight to Toronto for?
VH's selection of Toronto hotels is also a bit poor, but as I can get 10% off, maybe I'll just go for one of those anyway.
Thanks for any tips!

Mike.