People also don't live or structure their lives to satisfy those who had a written conversation and want the copies burned.

Well, they should. Permanent record of every small transgression or juvenile excess or stupidity is inhumane...

What's inhumane is making every small transgression into some stigma that should follow a person around their whole life. I don't think we fix that by erasing all traces of the transgression, which in many cases may be practically impossible.

It's not obvious to me whether changing the view on transgression and stigma is practically possible.

In my experience it's strongly tied to personal experience: if I committed a transgression in my past I'm going to be more understanding towards others doing the same (still depending on the nature of the transgression and my rationalization of it). It's also worth nothing that what constitutes a transgression changes with the times, and often the public seem to forget/ignore this fact and retroactively apply stigma and resentment.

No. I'm struggling to think of a reply better than "Obviously, not."

I think your statement was already implicit in what I was saying. We should move on to the next bit where I say "But..." and you counter it.