I use a script to create a dotfile with comments about a file, and an ls wrapper that outputs the comments if present for that reason as well.

My setup is very slowly converging on getting back some of the things I enjoyed about AmigaOS... The challenge of course is that simulating it without rewriting every piece of software and/or replacing the kernel will always be a leaky abstraction, but I can at least do it for the basic desktop and terminal experience...