I've got multiple versions of several files because publishers have figured out that one of the advantages of ebooks is that mistakes can be corrected and a new file uploaded and because I keep many of the old versions. So, the first thing I'm going to have to do is create a file to archive old versions.
After that, I'm going to want to rethink how the current versions are organized. The most logical way is alphabetically, by game name or system name, but this isn't exactly how I do it. Sometimes, it's by game name or system name. Sometimes, it's by publisher. Sometimes, it's by category.
So, while I have Apocalypse World in the folder for lumpley games, I have all of the Apocalypse World hacks in a folder called AW Hacks. The Fate folder is... let's just say complicated. The Cthulhu folder has a whole bunch of subfolders for Lovecraftian games, but it's also got, in the Pelgrane subfolder, folders for other Pelgrane games, like Time Watch. But, Hillfolk has its own folder, even though it's also a Pelgrane game. I've also got folders for some authors, like Jenna Moran and Greg Stolze and Dennis Detwiller. And various Bundles of Holding have their own folders, only sometimes put inside of other folders.
This means I need to figure out whether to go with more consistency or more familiarity, and if the former, exactly what kind of consistency I'm aiming for. Still, this is necessary, as I do want to re-catalog everything. There's a lot of stuff I get via Bits-n-Mortar or various Bundles or as freebies that I simply lose track of. I want to know what I already have.