[Milhouse]

I still need the redundant files in case of failures though.

They're not really required at all, you only have them because (IMHO) you're using the wrong tools for the job.

However I maintain Kodi systems for my parents and friends and they aren't all that computer smart.

Yep, so do I, and my parents and bothers are also not that computer smart which is why *everything* runs automatically so that neither I nor they need to do anything.

GUIs have their limitations, such as forcing you to "train" users to perform specific arcane tasks every once in a while (they always forget what you tell them when they need to eventually perform the actions), whereas scripts can run without any user intervention, automatically. You could even configure your systems so that maintenance tasks (assigning new artwork etc.) are performed as and when the system boots (you could run the tasks in the background so that Kodi startup isn't delayed). You might also want to think about sorting out some remote access, as this makes life so much easier... assuming your folks have internet access of course!

But hey, whatever you're most comfortable with.

If I change these to -discart.png and such will Artwork Downloader now add the filename-discart.png files?

No. Artwork Downloader has no support for movie-name prefix.

I'm sure there has to be a way to have it ignore the filename portion but I'm not sure the syntax. I'll play around and see what I can get to work.

I'm sure it's possible, but you'll be left with an unsupported forked addon that may or may not work well. Alternatively you could just run a script and forget about AD entirely.