So, it may sound stupid that I'm giving up $100 with no hope of getting anything back. But that's because the counterfactual is stupid, not me.

(Disclaimer: I'm going to use the exact language you used, which means I will call you "stupid" in this post. I apologize if this comes off as trollish. I will admit that I am also quite torn about this decision, and I feel quite stupid too.)

No offense, but assuming free will, you are the one who is deciding to actually hand over the $100. The conterfactual isn't the one making the decision. You are. You are in a situation, and there are two possible actions (lose $100 or don't lose $100), and you are choosing to lose $100.

So again, are you sure you are not stupid?