Calendar wise, I really hope I will be able to accept calendar invites from the iPhone. Thats something I have really hated about the Treo. I don't always have time to sync up, and its very annoying when out and about seeing a new calendar invite come through but not even be able to see what it is, or when it is. This drives me and my co-workers nuts, Steve if your listening. You could get all of them to buy it if it had calendar invite support directly on the phone (I am purchasing one regardless, but will be annoyed if I can't accept invites). Click to expand.lom.To answer your question.YES.the iPhone currently syncs Outlook Contacts and Calenders and it is two way information using iTunes as the conduit to Outlook. However, and I think this is where you and others are going.the iPhone does NOT work with Outlook Exchange service normally found at a work site.
So you would not be able to sync your work calender/contacts if it is on the Exchange Server. Sync two computers together is also not supported at this time as already stated. You can use the iPhone on two computers but only to do specific functions.
This is an old post, but syncing Mac Outlook with Google Contacts is still an issue. I'm stuck working with Outlook 15 with no sync. I'm stuck working with Outlook 15 with no sync. It will seem crazy but my solution was to sync on my phone, not my laptop. If you're using iOS 10.2 or earlier, tap Settings > iCloud. Check your Apple ID and make sure that you turn on what you want to update (Contacts, Calendars, or Reminders). On your Mac, choose Apple menu > System Preferences > iCloud. Check your Apple ID and make sure that you select what you want to update (Contacts, Calendars, or Reminders).
For example: You can sync music/videos using one computer and on another computer you can sync calender/contacts. But that still does not allow you to share data between two computers. Hope this answers your question.