They might be doing it on linux. I've had the same experience. Supposedly it's possible! I never managed to get around the DRM nonsense.
The part that eats my time is converting the subtitles from an image format (vosub/psg) to a text format (srt), since the image formats have never worked well for me on plex. SubtitleEdit is good but it still takes manual managing.
Edit: I forgot about the annoyance of finding a drive that works with ripping software, iirc there's only a couple that will without flashing firmware