Here's one way I look at it. You could spend countless hours meticulously going through every file and grouping, renaming, etc. Or. You could take time, create a script to automate it all for you. This does a couple things:

1. You get some experience learning how to script dealing with file organization
2. You save time since you're automating a lot of formerly time-consuming activities thus freeing up time to do other things.

Also:

I will also delete stuff that I've watched/played that I didn't enjoy. I've come to a realization there's no point archiving it if I'm never going to use it again.

BLASPHEMY!!!