Well ... I've been to the "cloud" and back. Fortunately I didn't lose major data but I did have to spend a couple of hours cleaning up.
I was beginning to wonder why new contacts I placed in my iPhone (or iPad) were not showing up in my Outlook contacts after syncing with my main machine. iTunes indicated that even though the cloud was in use that the PC should be getting the synchronization. Not so. Once I turned off the iCloud for the calendar and contacts they started syncing with the PC again. Oh well, I'll just have to be satisfied with it as-is for now. Fortunately I'm not an "executive" so I don't live and die by a list of a thousand contacts. It is, however, pretty annoying.
Outlook 2003 has been and, as far as I'm concerned, will continue to be my nerve-center when it comes to calendar, e-mail and contacts. (I have no need or interest in 2007/2010 which the iCloud control panel seems to require. Too bad). Over the years I've built a pretty large system of folders where I keep things so my i-devices (like them as much as I do) are going to have to be subservient to that system, not the other way around.
Maybe they'll fix some of this for iOS6. I can't help but think that I'm not alone here ... Office 2003 is pretty sweet and I'm sure there's a lot of people still using it. Just call us "ribbon haters" if you like. Nevertheless the Outlook file system is still pretty consistent into the new versions I believe and why Apple can't straighten this out is beyond me. The bottom line here is that it just doesn't work (not that I'm saying anything new).