I know this is old now but just wanted to make sure the info is captured in the thread
The transcoder errors in the log appear to be the same as those that started when Microsoft released a faulty update for windows 10 on 10th july 2016. They did correct it 6 days later but repetitive runs of windows updates were needed and also at some point the fix could only be applied via specific download from the windows update catalogue
Jul 21, 2018 18:11:29.733 [13736] ERROR - [Transcoder] [stream_segment,ssegment @ 040eedc0] Failed to open segment list 'http://127.0.0.1:32400/video/:/transcode/session/99e244ff-a82c-47f6-9857-a3250c74275e/ea040546-3f90-4e60-adfd-8bebdef7fd74/seglist'
Jul 21, 2018 18:11:29.748 [14984] ERROR - [Transcoder] av_interleaved_write_frame(): Unknown error
Jul 21, 2018 18:11:29.760 [13736] ERROR - [Transcoder] Error writing trailer of media-%05d.ts: Invalid argument
Jul 21, 2018 18:11:29.786 [13320] DEBUG - Jobs: 'C:\Program Files (x86)\Plex\Plex Media Server\PlexTranscoder.exe' exit code for process 15292 is 1 (failure)
The main forum thread that covered this issue was this