Originally Posted by FesterTreo
Yes. It makes perfect sense. I use Evolution (linux app with similar functionality to Outlook) on my home desktop. My primary email address is a pop account on my own web server, which I can't post a link to because the idiotic profanity filter thinks that my relatively common last name is a dirty word....
Anyway, I also have a google account for my contacts. Evolution can sync with both of those, and so can Outlook. So, set up outlook to sync his contacts with google. You don't even need a gmail account. You can set up a gmail contacts with your own email address. I've done it. This also has the added benefit of having all of his contacts backed up in an extra location.
Now outlook and the pre are syncing contacts and email with the same servers, and everything is in sync. You make a change in any of the 3 locations (Outlook/Pre/gmail) and it shows up in the other two on the next sync.
It's really a simple, effective and painless way to get the job done.
Task sync is another issue, but it looks like you've already read up on that one.