Best way to sync contacts with Mac OS X AND Windows AddressBook?

[Giaguara]

Alrighty, if I was Mac OS X only, syncing AddressBook data either manually or with iSync etc would do it and very easily.

But is there a good way to keep the contacts of Mac's AddressBook and Windows, say XP's Outlook in sync?

Or if anyone is actually keeping their AddressBook and Outlook contacts in sync, how do you do it?

I don't like using Outlook, or XP, but there is no choice for that.
Also the XP is on a physical PC - if I could simply use it as a virtual machine in Fusion, I'd simply drag and drop the new contacts to my AddressBook and that's it. I don't care to keep all contacts on Outlook or Windows Addressbook side either - but I want to add the new contacts to my AddressBook of Mac. Ideally without taking every single contact there manually.

Using Thunderbird etc Mozilla's horror named mail clients is not an ideal solution either. I don't want to import my several GB sized Outlook data to it only to export some contacts, and on the Mac side I don't want to move out of AddressBook's formats.

Any ideas?

Create a new XP virtual machine, sync from Outlook to Outlook Express etc between the physical and virtual Windows, then drag and drop between the virtual machine and the host Mac?
Or create a virtual machine on both sides, in Workstation and in Fusion, and use Ubuntu's AddressBook to sync to host and then sync the data between that, or even use the same virtual machine?
Or just keep something like DSL and minimum AddressBook on a USB thumbdrive and use that?
All the options I can think of are very manual... how to script it?

How do you sync 'em?

[Just_Kris]

I have used Plaxo as a conduit with marginal success. I use Outlook at work and Entourage at home. I made the huge mistake of "upgrading" to Entourage 2008 and lost the direct sync capability that I had with my Treo and Missing Sync. Now Entourage has to sync to ical, which then syncs to Plaxo, which then syncs to Outlook. And Plaxo will not sync the tasks in ical. There are way too many steps in that equation and I have sent more time than I care to admit trying to recover lost calendar items & rid myself of duplicate contacts.

Toss in the fact that I abandoned the Treo in favor of a Blackberry. I'm still looking for the holy grail of syncing. Outlook --> Blackberry --> Entourage. Should not be that hard!

[Satcomer]

The only way I think off my head is to use your Google account as a go between. On a Mac use some like Spanning Sync and use a similar program on your Windows box. There has to be a Windows shareware/freeware that can sync data to Google floating around.

[Just_Kris]

Spanning sync looks interesting. The most annoying thing is that none of the sync programs handle my 3 biggest concerns: calendar, contacts and task list. The Outlook/Google sync seems to work well for the calendar; Plaxo does a marginal job on the calendar & contacts but it only handles the task list in one direction (from ical/Entourage to Plaxo). And for some crazy reason, Apple mail does not delete hotmail and gmail items once downloaded! And the search continues.....

[Giaguara]

Oh forgot to add my two big dislikes - Entourage and google products.

[Just_Kris]

I'm really beginning to hate Entourage also. The 2004 version was ok but the 2008 version assumes that it is the end-all, be-all information management product. Why oh why Apple didn't integrate mail, address book and calendar, I will never understand.