The debug log doesn't show you playing any file - so doesn't help much. Please try again and when the screen goes black ssh in and run "pastebinit /storage/.kodi/temp/kodi.log", then post the URL.
I noticed you have the RPi VNC server installed, please disable or uninstall it, it uses the dispmanx grabber as well and might interfere.
BTW: Enable "wait for network" in the LE settings will fix the timestamp issue - kodi is starting before the network connection is up and at this point it didn't get the correct time from the NTP servers.
so long,
Hias