> what would a normal intelligent human do in this situation?

Problem is that this requires testing what actual "normal intelligent human" would do, because very often programmer has other ideas and UI/UX people have other ideas.

> A human would copy every file it could, maintaining a list of issues.

How do you know? From your idea what should be done instead of current version? I would not do it like you said.

Also, there are many reasons for transfer not succeeding and depending on a reason why transfer didn't succeed, you should make different decisions. sometimes reasons are not predictable by a program (a new file transfer method over pidgeons was transparently added to the system and "carrier attacked by predator" was not included in "how to handle this reason").