Here's the secret to moving your contact addresses from OutLook into Mac Mail.
1. Install Mozilla Thunderbird on your Windows PC
2. Import your address book into Thunderbird
3. Export the address book from Thunderbird into a LDIF file
4. Transfer the LDIF file to the Macintosh
5. Import the LDIF file within Mac Mail. There is a nice function that updates existing records, rather than create new ones.
The reason this is more effective than just exporting to a commma delimited text file from OutLook is that it effectively preserves any notes that you have written for the contact. Previously I tried to export directly....then went from OutLook to Excel...and then reimported; but the result wasn't satisfactory.
Now if I could figure out a way to synchronize the various address books...
As far as messages are concerned, however, they appear to be syncing up nicely. On the Mac, I created a new eMail account and defined it as an IMAP account. With IMAP you download only the headers of the mailbox messages; and it requires a live connection to the mail server. On the OutLook side, I just modified the properties of the existing eMail account to "leave messages on the server". Now I can see messages from either platform, or log in to the webmail interface for my master account.
As for calendars, I'm now using Google Calendar as the master calendar and subscribing to the Google calendar with OutLook's calendar and the Mac iCal. Doesn't all quite work as it should yet, but I think maybe I'm getting there.
Of course this should all be transparent and easy, right?