Re: Reasons NOT to upgrade?
"Application availability. Several of our key applications just won't run on Server 2012 = Yes they do, you just need server editions of said programs (or apps as you kids say)."
Let's see, what programs refuse to run on this new OS? considering I've been in this game for years, nothing much would be preventing it unless we're talking about a difference akin to NT4 vs 9x
Chances are, you haven't altered the security policies of said machine, otherwise you wouldn't be posting what you did.
"Linux is not an option either as good portions of the ancillary apps use .NET classes that are not in Mono."
Now you're going insane, why would you use something with .NET, seriously? MySQL is understandable but .NET, man I want some of what YOU are smoking.
"If you think that iOS is a server OS then can I please have some of what you are smoking?"
People can and do use iOS on servers, I am not talking about iPhone or iPad iOS here even though you might get that impression /facepalm.