Rasplex playing video playlist out of order.

My wife watches TV’s shows to sleep (drives me crazy, but I love her) We created one large playlist of all episodes of roseanne. She previously watched using a Playstation 3 client, but in an effort to make her plex experience a bit better I installed Rasplex on a Pi 3 I had hanging around. I added a small plugin to control it using a wiimote and everything was peachy. Or so I thought. It turns out that when she starts playing the playlist everything happens as normal, but at some undetermined point the playlist starts playing from number 1 and continuing from there. I tried re-creating the list just in case it was an issue with the playlist itself, but the problem seems to still re-occur.

I verified that shuffle was not being used in any of these instances.

I found what I believe to be the related error message, but I admit to not being 100% sure. The pastebin has the whole log. The excerpt below is the instances of the errors I found +10 lines on both sides. There were more instances of the error later in the logs.

https://pastebin.com/1m11jtk8

rasplex: 1.8
PMS:1.9.4.4325

01:02:41 T:1479156704 NOTICE: Creating video thread
01:02:41 T:1479156704 NOTICE: Opening stream: 1 source: 256
01:02:41 T:1479156704 NOTICE: Creating audio thread
01:02:41 T:1479156704 NOTICE: Opening stream: 2 source: 256
01:02:41 T:1758458848 NOTICE: Display resolution DESKTOP : 1920x1080 (1920x1080) @ 60.00 - Full Screen (16)
01:02:41 T:1537209312 ERROR: CCurlFile::Open failed with code 404 for https://192-168-1-242.7d5ad6d198834c4dbe159b42debe1379.plex.direct:32400/playQueues/559?window=50&X-Plex-Token=SECRETSTUFF
01:02:41 T:1963050896 WARNING: CreateFile, successfuly opened </usr/share/XBMC/addons/skin.plex/720p/DialogOk.xml> instead of </usr/share/XBMC/addons/skin.plex/720p/DialogOK.xml>
01:02:41 T:1758458848 WARNING: CRenderManager::WaitForBuffer - timeout waiting for buffer
01:26:09 T:1479156704 NOTICE: CDVDPlayer::OnExit()
01:26:09 T:1479156704 NOTICE: DVDPlayer: eof, waiting for queues to empty
01:26:09 T:1479156704 NOTICE: Closing stream player 1
01:26:09 T:1479156704 NOTICE: CDVDMessageQueue(audio)::WaitUntilEmpty
01:26:09 T:1437594592 NOTICE: thread end: OMXPlayerAudio::OnExit()
01:26:09 T:1479156704 NOTICE: Closing stream player 2
01:26:09 T:1479156704 NOTICE: CDVDMessageQueue(video)::WaitUntilEmpty
01:26:09 T:1758458848 ERROR: OMXPlayerVideo: Got MSGQ_IS_ERROR(-1) Aborting

01:26:10 T:1963050896 NOTICE: DVDPlayer: finished waiting
01:26:10 T:1963050896 NOTICE: DVDPlayer: Opening: plexserver://160e8b0fbec202b49489801dc637d6dec8da61dd/library/parts/6670/1505399710/file.m4v
01:26:10 T:1479156704 NOTICE: Creating InputStream
01:26:10 T:1479156704 NOTICE: Creating Demuxer
01:26:10 T:1479156704 NOTICE: Opening stream: 0 source: 256
01:26:10 T:1479156704 NOTICE: Creating video thread
01:26:10 T:1479156704 NOTICE: Opening stream: 1 source: 256
01:26:10 T:1479156704 NOTICE: Creating audio thread
01:26:10 T:1479156704 NOTICE: Opening stream: 2 source: 256
01:26:10 T:1758458848 NOTICE: Display resolution DESKTOP : 1920x1080 (1920x1080) @ 60.00 - Full Screen (16)
01:26:10 T:1741681632 ERROR: CCurlFile::Open failed with code 404 for https://192-168-1-242.7d5ad6d198834c4dbe159b42debe1379.plex.direct:32400/playQueues/559?window=50&X-Plex-Token=SECRETSTUFF
01:26:10 T:1758458848 WARNING: CRenderManager::WaitForBuffer - timeout waiting for buffer
01:49:38 T:1479156704 NOTICE: CDVDPlayer::OnExit()
01:49:38 T:1479156704 NOTICE: DVDPlayer: eof, waiting for queues to empty
01:49:38 T:1479156704 NOTICE: Closing stream player 1