“Let me now just give you the “why” in why I’m not supporting the protection of individual files with individual passwords. It’s because there is no good reason, from a security point of view. In fact, at best it doesn’t make it worse, but in most cases it will. It’s much better security to use one, strong password for all files.”
True, based on the way it would ideally be used, but in my case I send random private data to relatives via email, and some of them are computer illiterate to the point where they actively resist anything that seems “complicated” no matter how simply I try to describe it.
I send them emails with a known base password (never mentioned in email) and sometimes change it up by appending extra characters, with hints in email about those extra characters. This has worked well, but it’s mainly a limitation of their fear and low computer literacy. Many older people are so mistrusting of computers (and generally forgetful) that you can only get them to do one thing, one way, after years of trying. I installed the old version of AcCrypt on their machines and they are still barely aware of what it is, thinking it came with Windows, even.
As a programmer you are operating at a higher mental capacity and may not see how people could be that simplistic!