In order to honor what I said exactly I guess Trump has to win the 2020 election from this very moment barring any and all circumstances or "rules"..
If Trump doesn't win 2020 I lose basically no matter the reason, which is kinda a shit bet, but I'll take it if you feel like holding me to it..
Ok, how about this: let's call it a draw if Donald J Trump is not on the ballot in at least 26 states for any reason. That would reduce your risk of retirement or death, except if he dies between election day and the EC meeting. But this would take away your chance to win in another (very unlikely) scenario - if he's not on the ballot but wins via write-in.
What would you consider a reasonable deadline for the EC meeting? Is December 31 good enough, or should we make it January 31?
I like your contingency on the EC because what if Trump wins the EC but, the EC is abolished between now and then?
But I guess I would still loose if Trump lost because the EC was abolished..
I see all sorts of dirty tricks they could play..
Abolishing EC is almost impossible, particularly in time for the 2020 election as it would require an amendment to the constitution. I think we can agree that the constitution stays put, short of Martian invasion.