My two cents here. Yes it will scan if it notices a change or it will scan on the scheduled time you have set. You can force a scan on the library anytime you want.
Go to any library and click on the three dots. Then select scan library files. This will scan the whole library.
I would recommend that you do not set plex to prefer local metadata.
As for your other question
No Contributing artist does not map to either of those, it is a different tag. In your metadata picture you show Album Artist as Chic on one track named good times, and you also show that same name Chic as the Contributing Artist, and all the other tracks only have contributing artist. If you insert “Various Artists” into the Album Artist tag for every single song, that will put all the tracks under the various artists.
No it does not map. That is the Artist tag.
To make the files play nice with Plex you can approach this in two ways.
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You can use iTunes or mp3tag to go through each file and put “Various Artists” in the Album Artist tag, and put all your contributing artists into the Artists tag.
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Or you can leave the files as they are and put the music in the folder structure that Plex needs to see.
I know you mentioned you were using iTunes and would like to keep using. Whatever you do, keep in mind that if you are actively using iTunes, or another app at the same time as Plex, that is set to “manage your library” or “organize your library” any manual changes you make to Plex or the files, could get undone by another application especially if that other application moves things around from folder to folder. So if you are using iTunes make sure to check in preferences > advanced
If keep itunes media organized is ticked, then itunes will actively move things around as you add to your library or change things. If so then itunes will be your home base of sorts where you can manage your library and tag things and then let Plex do its thing. You can very easily use iTunes to “retag” your files and that should help Plex match up.
For example I have one compilation in my test library called summer hit mix. And it does not sort properly in my Plex Library. I can easily add the Album Artist Various Artist by going to the album three dots and selecting Album Info
Then put Various Artists in the Album Artist slot
A green check will show up hit OK.
To Check your individual artist which should be good if you let itunes manage. go to a track and to the three dots to the right, and select song info
The song artist should be here. So in your case you could copy the contributing artist tag into the artist tag if it is not there. Hit ok.
Plex should notice the change and auto scan. Just to be sure Plex caught the change. Go to the three dots, and scan library and then once that is done, Go to the three dots and tell Plex to Refresh Metadata. Be warned this rescan will rescan the entire library and pull metadata so things might move around.
That will help a little, but if you are going for perfection, you may need to plex dance. So after you make the changes do a plex dance it should then rack and stack things properly.
This is the tough part when you are moving from one to the other. I did the same thing as you for a while. I kept itunes for the family and then plex for travel. But over the last 2 years I have moved completely off of iTunes and only use Plex for music now. Be brave. and Good luck.
