“But suppose you were being recommended for, or applying for some high level job where they do background checks and gather that sort of information?”
Background checks are easy. So are single scope background investigations. You tell them everything. What you don’t want is to miss something and they find out about it. Or you don’t want to lie about something and they find out the truth. Simply tell them everything, absolutely everything and they will make a determination. Most of time that determination is that you were truthful and therefore trustworthy
It’s what I’ve never understood: If being investigated for a security clearance or a job position, just tell the truth. It will go much worse for you if they find you out in a lie, and after multiple investigations, the chances of remembering what lie you told when become impossible...