Outbound = VIA Rail. You could do VIA 1, but why bother? Its the same seat and you are on board 1.5 hours............barely enough time to eat, let alone enjoy the wine! Also, VIA Rail has comp wifi. There is also a comp shuttle to the terminal. Look for the phone outside the station.

Inbound, I agree the cnx. is way too tight. You could do the Greyhound (8:30 pm as I recall). If not, why not stay near the airport? Do you need the IHG stay for status? If not, I recommend the Sheraton Montreal Airport & a free shuttle. Save $$ on cabs and upgrade for lounge access.