I have in my library Season 8 of Friends and I have 5 episodes Optimized for TV.
I wish to optimize the rest of the episodes. When I click Optimize for TV I choose “Unwatched only” and uncheck the Limit to option (screenshot attached).
Check the Optimized Versions page. Sometimes a failed optimize will still result in an empty file being generated so PMS thinks it’s already been done and won’t run again. Delete them and try again.
Your logs show that you’ve enabled hardware transcoding, but PMS is not able to use your hardware. This could be causing the failures so might as well turn off that feature and see if that helps avoid this issue.
For the crash, I’m not sure what’s causing that. Could be all these failures causing a memory issue. If the failures stop with my suggestion above, then these may just automatically go away too.