Can I sync one iPhone via two computers (MacBook and Windows XP) using iTunes?

My idea is the following:
Sync one iPhone using iTunes installed on two computers:
from Windows XP:
* Outlook 2010 contacts
* Outlook 2010 calendar
* music
from MacBook:
* contacts
OR
from Windows XP:
* Outlook 2010 contacts
* Outlook 2010 calendar
from MacBook:
* contacts
* music
Can I do this?
How would I have to do the set-up?
Additional question: Can I buy apps from iTunes App Store on either of the two computers and having them downloaded automatically on the iPhone?

You can't. You can only sync with one library at a time. I is possible, though not recommended, to sync contacts with one computer and media with another. There is no way to sync contacts with more than one computer.
The best idea would be to sync it with your MacBook and the cloud, and sync Outlook on the PC with the cloud.
Since iCloud requires Windows 7, you would probably be best to sync contacts and calendars with Google or Yahoo.

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