Hi All,
I am new to this forum, but hopefully my 2 cents will be usefull for others.
First of all I don't like when people say 'you are stupid if you are using Outlook' etc. As some of people here pointed out there are some reasons for using Outlook and some people will like it more then the built in apps from Apple. I personally use Outlook for Mac 2011 because I like the way I can organize things, and lots of shourtcuts it provides (e.g. I can move messages to folders without touching the mouse - I prefer to use keyboard as I can touch type).
On the other hand what is annoying is that if in Spotlight I search for something that happens to be in the email then Outlook will not provide the preview for it, I cannot see the content of the message in the Spotlight. And this is the reason why I use both email apps, Outlook and the Apple Mail. Of course I use IMAP, not POP3, as I prefer to keep emails on the mail server. I saw a few posts from people about importing the .pst Outlook file from Windows to Outlook for Mac 2011. I tried that too and it fails - some mails were lots, some of them lost the attachements. The way I solved the problem was to upload my emails from the .pst file back to the server using IMAP protocol. That I did still on the Outlook for Windows. Now all my emails are in the cloud on the IMAP mail server. Of course I had to have enough storage on that server.
Going back to the initial problem of synching the calendar with the iCloud, I experienced the same, after turning on the iCloud all my events were gone from iCal and from Outlook. I figured out that when you turn on the iCloud this is not synchronization, rather iCloud takes all the events from 'on my mac' calendar and changes them to 'iCloud'. So in practice iCloud just snatches all events and moves them out of the local mac. As a result Outlook calendar will be cleaned as well. Now, in iCal you can turn on iCloud as one source of calendar events and these will appear in iCal. If you right-click on an event later on you can swich it to local mac - at which point the event should be brought back to your local mac and it should also appear in Outlook.
Summarizing, with iCloud you don't synchronize the events. If you turn on the iCloud it will take all the calendar events to the cloud, leaving nothing locally. Then in iCal you can use iCloud as a calendar source, similarily as you can use Google calendar as another source.
I think at the moment there is no way to make Outlook 2011 work with iCloud. What we should be expecting is to have Outlook be able to pull the calendars not only from the local mac but also from other sources like iCloud or Google.