I personally would not punt beyond mid Dec and even that is not as punt with a potential winter system next week. I think all modeling shows wintery weather here except the GFS....
I will take a shot. The air mass is coming out of Canada is quite cold as it moves into the Upper Mid West....the return flow from that ridge erodes it pretty quickly though so "stale cold"?
I know the feeling. I travel to Florida every few months and it gets stressful, in the winter, watching digital snow on models that I may miss. I fear I will miss the Blizzard of 2022!
On this subject, the Nam's have been too cool almost all summer and continue into the fall. Definitely something to watch for if they are they only ones calling for an icing event on a future system. Its been almost every day they are several degrees too cool.
There is a guy in the Pitt thread, @Ahoff with a similar predicament as you. Wants a "Get out of jail free" card on rooting for snow so they can travel.