re: iCloud + Outlook Equals IT Headache
I agree with your encouragement that end-users should work _with_ their IT departments, rather than behind the IT department's back. A little up-front discussion can save everyone a lot of hassle and headaches.
However, I do not agree that iCloud is a bad cloud, nor that Exchange is a better one. In fact, I don't think really consider Exchange much of a cloud at all. More like a fog bank. (And I don't mean that derogatorily ... it's just closer to the end user.)
iCloud is NOT an enterprise solution. Apple doesn't claim that it is, and -- as you point out with the Exchange conduit -- it doesn't behave like one.
But it's entirely possible -- probably even likely -- that iCloud will save some user's critical document that we, in IT, didn't even know existed. And us just asking the user, "Well, have you checked your backup that happens automatically via iCloud? It should be there." could allow IT to look like more of a helpful force within a company than one that's always highly restrictive and saying "no".
And iCloud could really be a god-send for entrepreneurs and super-small shops where back-ups are seldom performed otherwise.
In the end, there are pros and cons to most things that touch IT. iCloud is no different.