Sync to two calendars and address books?

I have a Mac at home with my calendar, contacts, music, photos, movies, etc. I have a PC at work with more calendar and contacts info. I tried to sync my iPhone with both - hoping to keep all three calendars in sync (I used to do this with my Treo 650, there were some hiccups but it generally worked).
The first time it seemed to work because lots of discrepancies popped up that needed to be resolved. No surprise there, I figured that would only have to be done once.
But now when I connect my iPhone to my PC it says it's synchronizing but it doesn't really do anything. None of the calendar or contact data is synced at all. It doesn't complain at all either. I reset the sync history and even deleted previous backups. iTunes on the PC did re-backup my phone but still didn't sync anything.
Oddly, iTues sees Outlook but my calendars and groups are not enabled for me to limit syncs to, say, my "work" calendar.
Here are some of my settings:
- Windows XP with Outlook 2003
- auto-sync is off
- set to sync only checked items
- On PC, the only syncs requested are under "info" tab
- haven't tried the advanced "replace info on this iPhone yet"
Any ideas?

Hi - I sync my home iMac and my work PC w/ XP to the iPhone daily.
First, make sure before you sync that the tab next to info (I can't look right now) has the calendar and contacts that you want to sync checked. It always works for me. When given the choice, you wants to select merge the data.
For calendar items:
. On the PC under Outlook -- you Mac calendar items will be merged into your Outlook calendar.
. On the Mac - your Outlook calendar items will be maintained separately.
For Contacts:
. On the PC - your Mac contacts will be merged into your Outlook contacts.
. On the Mac - your Outlook contacts will be part of your overall AB contacts. You can still, however, maintain separate groups.
Hope that helps.
iMac, PowerBook, MacBook, iPhones Mac OS X (10.4.10)

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Sync to two calendars and address books?

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