Tag issues when managing my own original Music files

Hi! I love plex and use it to manage my music library and listen on all my devices and love it. Recently, I’ve started DJing and making my own mixes. I use an Mp3tagging software to add titles, albums, art, etc to my mixes and I have been trying to upload them to plex. There are so many glitches when this happens, sometimes they load, sometimes it assumes an album is part of another album (even when it has it’s own album tag), and sometimes it doesn’t even add songs under my “artist” name.

I haven’t really had this kind of issue with other tags in other songs, so I don’t know what’s exactly going on behind the scenes that’s giving me all these errors. I was hoping you guys might provide some insight. I’ve tried so many things and the closet i’ve come to debugging the problem is that it if I delete the files and then copy then one by one to the library folder produces a new file each time (perhaps the time stamp of the “date created” becomes different). But this is very cumbersome and sometimes I want to add to old albums without deleting everything I have thus far and copying them back in.

Do you guys have any tips or suggestions on how to improve this? Also some way to list all my songs in one playlist by clicking my artist name without going thru each album would be very helpful. I cant seem to find a way to list all the songs by one artist in one window without having to select also an album.

Thank you!!

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