I remember one of the problems with running a Windows server was that if a fatal error occurred, there would be a crash dialogue and you would have to click "ok" - while on Linux the server would simply restart automatically without user intervention. (Unless the server freezes instead of a normal crash.) There's this parameter
-nocrashdialog which is meant for clients, but I have seen server owners using it in their start-up line so it might help (along with
-console naturally).
ServerDoc might also help, but not sure if it can cover all situations.
And then there's
ServerChecker - might also be worth checking out.
Maybe you already know all of this, but then there's the fun server being off-line since 20 hours.