I like how you visualize the pending pledge reduction while it's in the transitionary state. I think it would be nice if, given the amount of safety buffer present, the $10 were shown in a dull grey or something, and the $5 in gold. Whereas if I were about to derail tomorrow, the $10 would be gold and the $5 grey.
This is a principle that I try to employ in Complice whereever possible—never make the user have to consider if something is A or B, if the app already knows. An example might be "If you already have the Complice+Beeminder integration set up, go here. If not, go there" If the user is logged-in to Complice, then that "IF" question is something that should be handle by an if statement in the code, not by the user.