Wait till you see him up-close and personal with HD during the convention and subsequent debates. Stocks in Maybelline have skyrocketed in anticipation of the need for a lot of makeup.
Quick aside. I think the bet should start at the inauguration day. Texas Tech is going to be too good for me not to be on here this year.
No way on the D&D. Right after election day is when the fun starts. If the loser isn't denied that, the bet's meaningless. But I'll make this compromise: Loser self-bans for 3 months from D&D 24 hours after the race is called (that will allow for some gloating and a concession speech). Loser self-bans for 3 months from Hangout on date of your choosing.
Quick caveat before you respond: The ban needs to include at least one month of Texas Tech's season. This bet is supposed to hurt some.