Thanks, Squid for the response. I went through every docker container with a magnifying glass and found the issue! Turns out, I had the Plex Appdata config path pointed to a cache drive that didn't exist. I renamed it to the correct cache pool and voila! All those errors I experienced disappeared and my Plex library is available after every reboot. Thank you for your assistance!
***Warning to new guys who are using Unraid for Plex***
Setting the Plex AppData config path to the cache (mnt/cache/appdata/PlexMediaServer) WITHOUT a designated cache drive on your server (or one that is named differently that doesn't contain your Plex appdata) will cause you to lose your Plex settings on every reboot and cause a host of other problems (rootfs maxed, webUI unresponsive, uninitialized csrf_token, etc.).
Make sure your Plex AppData config path is named correctly if you're using a cache drive/pool. In my case, I had the path as : mnt/Cacheone/appdata/PlexMediaServer.
After realizing the C is capitalized in that path, when my cache pool isn't, caused all my issues. I simply changed the WRONG path from: mnt/Cacheone/appdata/PlexMediaServer to the CORRECT path: mnt/cacheone/appdata/PlexMediaServer.