Hehe, I used to create a folder as some variant of "Old" and move everything in my downloads folder into it once or twice a year, and with a lesser frequency my documents. At one point when I realised this had got about 10 levels deep, I switched to yyyy-mm format directories instead of nesting them.

I also used to back up other PCs to each other somewhat regularly, and sometimes I'd end up with those files back on the original PC in a backup of another. Fortunately, when I switched to borgbackup on Windows as well [1], this massive reduplication of files became a solved problem.

[1] borgbackup doesn't officially work on Windows, but I run it in WSL which does reasonably well for all the files I really care about (i.e. the stuff I've made). When they have particular unusual characters in the filenames, it throws up a warning for that file every time, but otherwise seems fine. I've never bothered investigating whether those particular files restore to the correct filename, because I know I've also backed up the zip file those files have come from and it's just accidental that I've backed up the extracted files as well.

I still have a bunch of these called "FromOld".