This question came up recently: "I have Birthdays and other appointments in my Outlook calendar and I can't figure out how to import them into Windows Live Calendar. I have the Outlook Connector installed. I would like the info on my Windows Mobile 7 phone."
This is actually easy.
To copy (or move) the appointments from your current Outlook calendar to the Hotmail calendar folder in your profile, switch to a list view, select all then either drag or use the Move to command to move (or copy) the items to the Hotmail Calendar folder. You can do the same with your contacts so they sync with the phone.
You can use the same method to move (or copy) calendar and contacts between your default calendar and the iCloud calendar.
If you need a tutorial, we have one at Merging Two Calendar Folders
Published Nov 1 2011