Using https://github.com/deevus/docker-plex-remote-transcoder I've made some updates to get the ssh working.
But the other issue I found (after alerting prt.py to add logging was that it was getting an error:
ssh: /usr/lib/plexmediaserver/lib/libcrypto.so.1.0.0: no version information available (required by ssh)
ssh: relocation error: ssh: symbol ENGINE_load_builtin_engines, version OPENSSL_1.0.0 not defined in file libcrypto.so.1.0.0 with link time reference
To fix this, I can actually remove /usr/lib/plexmediaserver/lib/libcrypto.so.1.0.0 and everything seems to go...including the ssh via python.
The same library is also in
/lib/x86_64-linux-gnu/libcrypto.so.1.0.0
Thoughts on how I might fix?