Of course, after toiling with this for weeks, I was able to figure out a workaround to my problem as soon as I asked the question on the forums. The way I had my external setup was:
and this was causing problems for some reason. I changed the setup to this using a USB Y cable:
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external -> powered hub
external -> raspberry pi
and I am now able to stream via DLNA f̶l̶a̶w̶l̶e̶s̶s̶l̶y̶. (See below).
I still have one problem though and that's with transferring files to and from the external drive over samba. I mostly think this might be a network problem as file transfers in my network usually range around 2-3 MB/s, but to the external drive it's even slower at ~845 kB/s for reads on large files and even slower with writes.
UPDATE: I'm still losing connection through DLNA and get an error on my tv's client saying "Device has been disconnected." I checked my dmesg again and the USB message above is NOT present. This occurred about halfway through an episode of anime and also occurs if I leave the client paused for a while