I believe this is the reason the 'Application Initialization' module does not work, as it appears the server does not bother to spin anything up until the first request, causing it to fail.
The error produced on every first request is:
HTTP Error 500.21 - Internal Server Error
The specified handler mapping is incorrect.
Detailed Error Information
Module ManagedPipelineHandler
Notification ExecuteRequestHandler
Handler ExtensionlessUrlHandler-Integrated-4.0
Error Code 0x00000000
I have tried the .NET repair instructions here: https://msdn.microsoft.com/en-us/library/hh168535(v=nav.90).aspx
and I've tried uninstalling/reinstalling .NET, but it seems to behave like this no matter what.
The primary reason this is annoying is the website and anything that needs to be started with it will only be started after the 2nd request.
Edit: It might be worth noting that in my "Turn Windows features on or off" menu, I only have an option to enable "ASP.NET" as oppose to "ASP.NET 4.5" as many other posts have suggested would be there. Evidently reinstalling .NET did not make this appear.