I have a fairly large Plex library that's 100% legal. - Legal music from iTunes and AmazonMP3. - Ripped discs using MakeMKV. - A rigged-up pipeline of tuning

I have a fairly large Plex library that's 100% legal. - Legal music from iTunes and AmazonMP3. - Ripped discs using MakeMKV. - A rigged-up pipeline of tuning TV using an HDHomeRun, recording with MythTV, and a custom script to invoke Myth's commercial skipper, remove the commercials (using avconv), and rename according to Plex's desires. I used to have it compress the files down, but I let Plex do that on sync/play, since it'll usually have to transcode anyway. The first is super easy and definitely legal, no matter where you live. There may be some legal issues around breaking the DRM when you rip a disc, and it's not 100% dead-simple (some DVDs have weird structures). The third requires some pretty substantial babysitting.