> I wonder in the discussions surrounding these sorts of things (Right to be Forgotten, etc) if the issue isn't that there should be a right to be forgotten but rather that culturally we should be far far more tolerant of people fucking up. It feels like the perception of how much the average member of society transgresses its rules is totally out of sync with reality, though this may be by design to create space for exploitation.

That's "perfect being the enemy of the good" logic. Your solution might be more ideal in some sense, but it's also not realistic to implement. It's not too much different than saying the real issue is that we have crime in the first place. After all, if we didn't have crime, we wouldn't have police nor mugshots being albatrosses for some people.