I've had to resort to the "bridge" method.
This gets a little complex, but stay with me.
I use a product called Cardscan as a tool for importing contact details (it can scan business cards as well as let you manually enter addresses) This only runs on a PC (in my case a desktop running XP) Now I also run two laptops, a Tosh also running XP and a PowerBook G4 running OS X (10.3)
I use Outlook as a mail app and also want all my contact/apps etc "sync'd"
It gets worse, I also have an iPAQ and a "Smart" phone. I got sick and tired of numbers/adresses being on one device but not the other/s.
Here's how it works.
CardScan has a web service where you can store your database, I use this to sync two versions of CardScan, one on each XP machine. The local CardScan then sync's with Outlook on both machines. Outlook syncs with iPAQ via Active Sync (and with SonyEricsson CellPhone via supplied app) I use PocketMac to sync iPAQ to Entourage on the Powerbook.
That's appointments and contacts taken care of.
As far as mail is concerned, all devices point at the same accounts (4 email accounts) all are set to "leave copy on server" apart from the desktop machine which is set to download and delete very seven days (on a Sunday)
They all sync (with the correct rules in place) in a few minutes. I now know I have the same mail/contacts/apps on
A desktop
A Tosh (XP)
A Mac
An iPAQ
and a Sony Ericsson P910i
(with a back up of the contacts database on a third party web server)
PS One thing that did prove essential was a good "duplicate scanner" I use an Outlook plugin from "You Software" to scan both copies of Outlook for duplicate contacts/appointments/mail etc.