Rail Freak, I do not have suggestions but I want to let you know that I just booked my trip on the Canadian. I am leaving Toronto on 12/3/11
. I have also booked my return from Seattle with AGR points (the same route as you), CS, CZ, CL and SM.
I have not yet booked the Meteor to NYP and Maple Leaf to TWO. I have communicated with Alan and asked him for suggestions (other than spending an arm and a leg in New York). He mentioned staying overnight near Newark airport or Tarrytown, NY or Albany.
Even if the SM is late, you should have enough time between the SM and the LSL. If it is real late, then you could stay overnight in the city (or near Newark airport) and catch the Maple Leaf in the morning. Also there might be later Empire Service trains that would get you to SDY.
The AGR agent with whom I spoke on the phone just minutes ago is in PHL. She mentioned the snow this weekend, but did not think it would affect the trains, but might affect planes.
I can relate to your worrying - since I worry about everything - especially things over which I have no control.
Hopefully everything will go well - I am looking forward to a detailed trip report.
Again, thank you for all your assistance with plans.
BTW - VIA just posted its express deals for the first week of December a few hours ago.