Let's say I mod flag an off-topic bounty question for closure shortly after the bounty is added. The question is not answered, the bounty expires, and the user deletes the question. Deleting the question would not invalidate the mod flag, and at some point a mod would come along, see my flag, see that the question had been self-removed by the OP, and mark the flag as handled (usually "helpful").
Now that we have the ability to retract flags, I was reviewing my open flags and saw that a mod flag was still pending on a deleted bounty question. Since the question had been deleted, I retracted the flag since it was no longer necessary.
Should I be keeping track of my pending flags and retracting any that are no longer valid? Will I be penalized (with a declined flag) if I don't retract any of my obsolete flags?
I understand that this is kind of a specific example, and I also understand that any flags on borderline link-only answers that are edited into shape outside of the review queue will likely be declined.