@bubbascant based on your last logs, you’re running an older PMS version 1.41.5.9626-9ba082670. Could you please update your PMS to either the latest public release 1.42.2.10156 or install the latest beta release 1.43.0.10389. I’d be more interested if you could run the beta release for a bit as there is a specific PlexAmp fix around the transcoder.
Though I’m not sure how related the original issue for this 
fix is to the issue in this thread, but it would still be good to be running a newer version of PMS.
