Dedicated Server crash at startup, Assertion failed

Looking at your first log your game’s executable appears to be pretty involved in the call stack, as all of the plugin modules appear to have already loaded that doesnt seem to be the issue either.
You should try attaching a Visual Studio debug session to the process or loading the .dmp file emitted into Visual Studio so you can check the call stack for what is actually causing the crash. (the logs aren’t very transparent). If you have built, cooked, and packaged the server you should also be able to run the dedicated server directly from visual studio by switching the solution configuration in Visual Studio from Development Editor to Development Server.
Happy Hunting,
-Spiris