What does 'charitable' mean here? Generous towards what person or point of view? As you say you have conclusively proved that there is a non-zero probability of there being problems, the use of 'might' is already trying to persuade that this possibility is next to zero.
Yes, of course. If the case is reasonably likely to occur in the real world and have real world impact, that is. And I would assume that the GNU grep developers would agree with me.
I think that is a very reasonable position to hold. It would only be the rejection of plausible cases, on the basis of no actual case having been uncovered, that I would take issue with. When assessing the downside of a proposal, there should not be much, if any, difference between how highly plausible and certain consequences are assessed.
If we could prove there would be no downside, then plausible problems could be ignored as merely hypothetical, and there would be no need to posit offsetting benefits. The question the GNU grep developers might want to consider is whether the supposed upside will have sufficient material consequences for their purposes.