It may had been that Ubuntu ignored the
-f portion of the install command. I just ran this to see if the command is not catching and it is indeed reading it.
quickbox:~# apt-get install -y -f --only-upgrade plexmediaserver
Reading package lists... Done
Building dependency tree
Reading state information... Done
plexmediaserver is already the newest version.
0 upgraded, 0 newly installed, 0 to remove and 0 not upgraded.
I'll need to have this ran against a few different scenarios to ensure it's a valid bug and not just a momentary hiccup.