My folder structure (Linux, by the way). Since the tags are in good shape, this isn’t all that important:
Music
Classical <--(Plex "Classical" Library points here)
Beethoven <--(composer)
9 Symphonien <--(album title)
01 - Symphony No 1 in C major op 21; 1. Adagio molto-Allegro con brio.flac
Bach
Dvorak
Popular <--(Plex "Popular" Library - all non-classical - points here)
Pop
Michael Jackson
Dangerous
01 - trackname.flac
Celtic
New Age
Various Artists
For ID3 tags, I used to use EasyTag, but it doesn’t handle all possible tags, so I recently started using Puddletag, which looks and operates very similarly to MP3Tag for Windows. I spent several months with EasyTag going through all my music (that’s only around 5300 tracks, small compared to some) to get the tags right. Now I only occasionally do things when I notice something I missed, or when I get new music.
When I acquire a new CD, I use Asunder to rip it. Asunder queries freedb.org to get artist name, genre, and track names. I correct any errors I see in Asunder before starting the rip. Purchases from Amazon I look at in Puddletag, but they’re usually already tagged in pretty good shape.
Then Puddletag to look at tags not exposed in Asunder (preparing for when Plex hopefully expands ID3 support) and make sure they are correct.
If I can’t find a decent-quality image of the CD cover, I’ll throw the CD cover on my scanner and make my own.
I use the OS’s file manager to move the folder (named for the album) under the Artist’s (or Composer’s) folder, then update the library in Plex.
I buy maybe 2 or 3 albums per year, so I don’t do this enough to warrant more automation than this.
how do you handle situations where you might have the same album multiple ways such as MP3 and FLAC versions of the same album?
I don’t. Well, I do, but only because I have to convert everything to MP3 for my car stereo. But the duplicates are not monitored by Plex. I can’t imagine why I would want Plex to care about that.