So I thought the problem was with the iOS apps so I also posted over there, but out of exasperation I removed the Server entirely, reinstalled it, and then for a little bit content played and then following a restart it no longer does, it opens as if it is going to play and then closes the player window and puts like a "restart" icon. I don't know if this helps but I copied this from the logs, not sure where else to look. Any ideas would be greatly appreciated.
Update: so I just tested the files remotely over 4G and they work fine so it seems to be an issue when on my home WiFi so I have to think it is a server config issue I am not seeing. So, I was reading another iOS10 post and I almost forgot I was running public beta iOS10, anyone else not able to play on their home network but can play remotely with iOS 10? Server Mac is still running El Capitan. Any ideas now?
ug 08, 2016 14:25:46.079 [0x7000006b8000] ERROR - CERT: Error in TLS handshake: sslv3 alert certificate unknown
Aug 08, 2016 14:25:46.096 [0x700000323000] DEBUG - Request: [192.168.2.146:52634] GET /video/:/transcode/universal/decision?X-Plex-Client-Profile-Extra=add-transcode-target%28type%3DmusicProfile%26context%3Dstreaming%26protocol%3Dhls%26container%3Dmpegts%26audioCodec%3Daac%29%2Badd-direct-play-profile%28type%3DmusicProfile%26container%3Dmp4%26audioCodec%3Dalac%29&X-Plex-Token=xxxxxxxxxxxxxxxxxxxx&audioBoost=100&directPlay=1&directStream=1&location=lan&maxVideoBitrate=200000&path=/library/metadata/7&protocol=hls&subtitleSize=100&subtitles=auto&videoQuality=100&videoResolution=1920x1080 (8 live) TLS GZIP