Alright, here's what I'm thinking of shooting for (and it'll require a reschedule, but I should have the points for it):
OSC-CHI (paid): December 26
CHI-SEA (points): December 27-29
SEA-Vancouver: December 29
Canadian Vancouver-Toronto: December 30-January 3 (I checked and this is a running date)
Maple Leaf, Toronto-Buffalo (cash): January 4
Lake Shore Limited, Buffalo-NYP (points): January 5
Silver Meteor, NYP-RVR (points): January 6
The latter two would ideally be "points-ed" together, as the layover is less than 24 hours. Yes, the LSL does come into NYP on one day and the SM leaves the next, but the LSL's arrival is late enough to preclude a "same day" departure. My alternate plan would be:
VIA, Toronto-Montreal: January 3
Adirondack, Montreal-NYP: January 4
Silver Meteor, NYP-RVR: January 5
Finally, I can always run a CZ-CS routing.
All of the Canada-US crossings are a ham-handed mess if you want to go past NYP given the arrival times. Yes, I am very much cursing the downfall of the Montrealer (among other trains) right now.