My iTunes only syncs my calendar and contacts on the second sync, why?

When I sync my Outlook Calendar and Contacts with iTunes, I noticed the first sync does the backup but doesn't sync the calendar and contacts. I need to click sync a second time and then it syncs my calendar and contacts. How do I set it up where it syncs everything including cal/contacts on the first sync?
Second Question: From when I had MM, I noticed it shows Work, Home, and Calendar under my Calendar. I want to consolidate and only have Calendar. Is there a way to consolidate all 3 and delete Home and Work?
iPhone 3G
Vista
iTunes 8.0.2.20

Blondebrit,
Try iPhone/iPod touch: Resolving duplicates and removing all contacts/calendars/bookmarks with MobileMe.
;~)

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