Plex not sync'ing all the way

Server Version#: 1.18.0.1913
Player Version#: 4.8.4
PMS is working for TV shows but not movies to my iPAD Mini Gen 1 running iOS 9.3.5 and Plex 6.2.

I have tried initiating the sync from my iPad and from the web client. It seems like I can only get 2 shows sync’ed to my iPad or 2 movies and then nothing else. I have 6-8GB free of storage space when there isn’t anything sync’ed. I have a sample of the logs below. I don’t know if this is an issue w/ the iPad ( I assume it is since it works on my Android devices running Android 9.

Oct 13, 2019 19:19:21.772 [63788] VERBOSE -  * X-Plex-Device-Name => Andrew's iPad Mini Gen 1
Oct 13, 2019 19:19:21.772 [63788] VERBOSE -  * X-Plex-Device-Name => Andrew's iPad Mini Gen 1
Oct 13, 2019 19:19:21.772 [63788] VERBOSE - It took 0.0 sec to serialize a list with 0 elements.
Oct 13, 2019 19:19:21.773 [15632] DEBUG - Completed: [10.150.1.101:65384] 200 GET /sync/transcodeQueue (12 live) TLS GZIP 2ms 397 bytes (pipelined: 135)
Oct 13, 2019 19:19:22.088 [15628] VERBOSE - Comparing request from 10.150.1.101 against 10.0.0.0/255.0.0.0
Oct 13, 2019 19:19:22.088 [15628] VERBOSE - Auth: We found auth token (xxxxxxxxxxxxxxxxxxxx), enabling token-based authentication.
Oct 13, 2019 19:19:22.088 [15628] DEBUG - Auth: authenticated user 1 as andrewm659
Oct 13, 2019 19:19:22.088 [15628] VERBOSE - Auth: Came in with a super-token, authorization succeeded.
Oct 13, 2019 19:19:22.089 [62956] DEBUG - Request: [10.150.1.101:49504 (Allowed Network (Subnet))] GET /sync/45B8CCD8-6F8D-429A-B9BA-753C73FC9432/library/files/850/file.mp4 (12 live) TLS Signed-in Token (andrewm659)
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * Host => 10-150-1-50.e61e3439811e46909309b8200b09fe16.plex.direct:32400
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * X-Plex-Token => xxxxxxxxxxxxxxxxxxxx
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * X-Plex-Product => Plex for iOS
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * X-Plex-Platform => iOS
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * X-Plex-Device-Screen-Resolution => 1024x768
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * X-Plex-Http-Pipeline => disable
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * X-Plex-Version => 6.2
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * Connection => keep-alive
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * X-Plex-Model => 2,5
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * X-Plex-Client-Identifier => 45B8CCD8-6F8D-429A-B9BA-753C73FC9432
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * X-Plex-Device => iPad
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * Accept-Encoding => 
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * X-Plex-Sync-Version => 2
Oct 13, 2019 19:19:22.089 [62956] VERBOSE -  * X-Plex-Username => andrewm659
Oct 13, 2019 19:19:22.090 [62956] VERBOSE -  * Accept => text/xml,application/xml
Oct 13, 2019 19:19:22.090 [62956] VERBOSE -  * X-Plex-Device-Screen-Density => 1
Oct 13, 2019 19:19:22.090 [62956] VERBOSE -  * User-Agent => PlexMobile/6.2 (iPad; iOS 9.3.5; Scale/1.00)
Oct 13, 2019 19:19:22.090 [62956] VERBOSE -  * Accept-Language => en-US;q=1
Oct 13, 2019 19:19:22.090 [62956] VERBOSE -  * X-Plex-Supported-Commands => abort,changeQuality
Oct 13, 2019 19:19:22.090 [62956] VERBOSE -  * X-Plex-Provides => client,controller,sync-target,player,pubsub-player
Oct 13, 2019 19:19:22.090 [62956] VERBOSE -  * X-Plex-Platform-Version => 9.3.5
Oct 13, 2019 19:19:22.090 [62956] VERBOSE -  * X-Plex-Device-Vendor => Apple
Oct 13, 2019 19:19:22.090 [62956] VERBOSE -  * X-Plex-Device-Name => Andrew's iPad Mini Gen 1
Oct 13, 2019 19:19:22.090 [62956] VERBOSE -  * X-Plex-Device-Name => Andrew's iPad Mini Gen 1
Oct 13, 2019 19:19:22.091 [62956] VERBOSE - [IDLE] Adding (0->1) work item http_download - /sync/45B8CCD8-6F8D-429A-B9BA-753C73FC9432/library/files/850/file.mp4?X-Plex-Device-Name=Andrew%27s%20iPad%20Mini%20Gen%201
Oct 13, 2019 19:19:22.091 [62956] VERBOSE - [IDLE] * http_download - /library/metadata/852/thumb/1570815895?X-Plex-Device-Name=Andrew%27s%20iPad%20Mini%20Gen%201 - 1 active item(s)
Oct 13, 2019 19:19:22.092 [62956] VERBOSE - [IDLE] * http_download - /player/proxy/poll?deviceClass=pc&protocolVersion=3&protocolCapabilities=timeline%2Cplayback%2Cnavigation%2Cmirror%2Cplayqueues&timeout=1&X-Plex-Product=Plex%20Web&X-Plex-Version=4.8.4&X-Plex-Client-Identifier=zxauvlnrmbgky9r4t0gc3t1a&X-Plex-Platform=Firefox&X-Plex-Platform-Version=69.0&X-Plex-Sync-Version=2&X-Plex-Features=external-media&X-Plex-Model=bundled&X-Plex-Device=Linux&X-Plex-Device-Name=Firefox&X-Plex-Device-Screen-Resolution=1366x582%2C1366x768&X-Plex-Token=xxxxxxxxxxxxxxxxxxxx&X-Plex-Language=en - 1 active item(s)
Oct 13, 2019 19:19:22.092 [62956] VERBOSE - [IDLE] * http_download - /sync/45B8CCD8-6F8D-429A-B9BA-753C73FC9432/library/files/850/file.mp4?X-Plex-Device-Name=Andrew%27s%20iPad%20Mini%20Gen%201 - 1 active item(s)
Oct 13, 2019 19:19:22.092 [62956] ERROR - Couldn't find the file to stream: C:\Users\TV\AppData\Local\Plex Media Server\Cache\Transcode\Sync+\35691173\84\850.mp4
Oct 13, 2019 19:19:22.092 [15632] DEBUG - Completed: [10.150.1.101:49504] 404 GET /sync/45B8CCD8-6F8D-429A-B9BA-753C73FC9432/library/files/850/file.mp4 (12 live) TLS 3ms 240 bytes
Oct 13, 2019 19:19:22.278 [15628] VERBOSE - Comparing request from 10.150.1.101 against 10.0.0.0/255.0.0.0
Oct 13, 2019 19:19:22.278 [15628] VERBOSE - Auth: We found auth token (xxxxxxxxxxxxxxxxxxxx), enabling token-based authentication.
Oct 13, 2019 19:19:22.278 [15628] DEBUG - Auth: authenticated user 1 as andrewm659
Oct 13, 2019 19:19:22.278 [15628] VERBOSE - Auth: Came in with a super-token, authorization succeeded.
Oct 13, 2019 19:19:22.279 [61136] VERBOSE - [IDLE] Removing (1->0) work item http_download - /library/metadata/852/thumb/1570815895?X-Plex-Device-Name=Andrew%27s%20iPad%20Mini%20Gen%201
Oct 13, 2019 19:19:22.279 [61136] VERBOSE - [IDLE] * http_download - /player/proxy/poll?deviceClass=pc&protocolVersion=3&protocolCapabilities=timeline%2Cplayback%2Cnavigation%2Cmirror%2Cplayqueues&timeout=1&X-Plex-Product=Plex%20Web&X-Plex-Version=4.8.4&X-Plex-Client-Identifier=zxauvlnrmbgky9r4t0gc3t1a&X-Plex-Platform=Firefox&X-Plex-Platform-Version=69.0&X-Plex-Sync-Version=2&X-Plex-Features=external-media&X-Plex-Model=bundled&X-Plex-Device=Linux&X-Plex-Device-Name=Firefox&X-Plex-Device-Screen-Resolution=1366x582%2C1366x768&X-Plex-Token=xxxxxxxxxxxxxxxxxxxx&X-Plex-Language=en - 1 active item(s)
Oct 13, 2019 19:19:22.279 [61136] VERBOSE - [IDLE] * http_download - /sync/45B8CCD8-6F8D-429A-B9BA-753C73FC9432/library/files/850/file.mp4?X-Plex-Device-Name=Andrew%27s%20iPad%20Mini%20Gen%201 - 1 active item(s)
Oct 13, 2019 19:19:22.279 [61136] DEBUG - Request: [10.150.1.101:65384 (Allowed Network (Subnet))] GET /sync/45B8CCD8-6F8D-429A-B9BA-753C73FC9432/status (11 live) TLS GZIP Signed-in Token (andrewm659)
Oct 13, 2019 19:19:22.279 [61136] VERBOSE -  * Host => 10-150-1-50.e61e3439811e46909309b8200b09fe16.plex.direct:32400
Oct 13, 2019 19:19:22.279 [61136] VERBOSE -  * X-Plex-Token => xxxxxxxxxxxxxxxxxxxx
Oct 13, 2019 19:19:22.279 [61136] VERBOSE -  * X-Plex-Product => Plex for iOS
Oct 13, 2019 19:19:22.280 [61136] VERBOSE -  * X-Plex-Device-Screen-Resolution => 1024x768
Oct 13, 2019 19:19:22.280 [61136] VERBOSE -  * X-Plex-Platform => iOS
Oct 13, 2019 19:19:22.280 [61136] VERBOSE -  * X-Plex-Http-Pipeline => infinite
Oct 13, 2019 19:19:22.280 [61136] VERBOSE -  * X-Plex-Version => 6.2
Oct 13, 2019 19:19:22.280 [61136] VERBOSE -  * Connection => keep-alive
Oct 13, 2019 19:19:22.280 [61136] VERBOSE -  * X-Plex-Model => 2,5

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