I was also curious why so many css files? Is it just for better management, is it to keep one file from being huge or is there an actual technical reason based on the structure of the script?
Thanks

./ext/vendor/name/language/en/override_common.php
core.user_setup_after
and load your language file. Everything you have there will overwrite language keys previously loaded.Nowadays there's actually little to no need for editing core files. I would say that almost anything that needs customizing can be accomplished through extensions and events including things like changing behavior or what is returned for language keys. Plus adding a CSS override is as easy as adding a CSS file to the same extension that gets appended to the header and override classes there as needed. This is what I do for all clients that need customized style changes for their forums.
There are also events which allow to create mini-extensions that can override things for "that and this and there", not only language.
Not if you ever want to modify that file - although there are online utilities that will "unminify". Also if it part of an extension then both files should be in the extension.