Server Settings Unavailable & Matching not working

Server Version#: plexmediaserver_1.20.1.3252-a78fef9a9_amd64
Player Version#: Irrelevant

Alright, so I’ve been running my server - without issue - for several years now. After a recent upgrade, server settings appear as unavailable and matching is no longer working. I was able to hunt down the cause as this:
ImportError: /home/######/.local/lib/python2.7/site-packages/lxml/etree.so: undefined symbol: PyUnicodeUCS4_DecodeLatin1

Googling around, it’s clear I’m not the first person to run into this issue, but no genuine fix has been presented. It can be resolved by moving the .local/lib/python2.7 directory elsewhere, but obviously that’s not an ideal solution. This combined with the fact that it only started happening recently leads me to imagine it has something to do with how plex is interacting with the local python install, and - more importantly - why (it’s always been my understanding that plex comes bundled with it’s own python due to certain dependencies, especially relevant now with python2.7 reaching its EOL).

Permissions on both /var/lib/plexmediaserver and /usr/lib/plexmediaserver are user:group, with user being the user running the plex server. I don’t want to change this user, and I have my doubts that permissions are the problem but I’m willing to try just about anything.

python --version
Python 2.7.13
python2 --version
Python 2.7.13
python3 --version
Python 3.5.3
python3.7 --version
Python 3.7.3

My first thought was that this last one could be related as I recently installed python3.7 for a project, but after completely purging that install from the system and rebooting, the problem persists, so that’s not it. OS is Debian stretch.

Have any of you seen anything like this before?

EDIT: Before anyone asks, I have already done a complete reinstall of the plex server, just in case. I mean a sudo dpkg --purge plexmediaserver and a reinstall. Very inconvenient, but I had to be sure. It didn’t help.

EDIT 2: Unless I’m misunderstanding something, it’s looking more and more like Plex is deferring to the local python2.7 installation, presumably not compiled with --enable-unicode=ucs4. I’ve half a mind to recompile it with this option, but this is repeatedly advised against since it would be modifying the default python install, and who knows what other options it may have been compiled with.

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