Sorry, I don’t understand your first clause - lose the ability to do what?
No, $100 would be the correct amount for a legit (akratic) derail. But a lot of the time I’ll be derailing non-akratically, and those are non-legit, so I can’t bee paying $100 for those times. The pledge is for akratic derails.
I’m deciding (upfront) that on days where I don’t do half the things, I’ll pay $100 for an akratic derail, but if, say, I had client meetings or appointments or had to be in court, that’s not an akratic derail. And since the “real” deadline is the end of the day, if I do it by the end of the day, that doesn’t count as a legit derail either.