So I got tired of following my post on how to update Plex Playlists and decided to just download the Media Monkey app on my phone and use that to listen to music locally. The problem was, I couldn’t get my phone to show up as a device in Media Monkey! I eventually found the fix according to this thread. Thank god for the internet!
Go to Device Manager (win+r => devmgmt.msc)
Find your phone under “Portable Devices”
Choose to “Pick a Driver” and point to the second one instead of the first and it should allow your phone to show up in Windows Explorer properly.