Outlook not sync contacts with changed "file as" field?

I am syncing contacts and calendar from Outlook on my office PC (and everything else from Mac at home). I have a very large contact list and have noticed that a number of key contacts have not synced. It appears that any contacts with a changed "file as" field have not been syned (e.g. contact entry of "Daniel Smith" with "file as" field altered in Outlook to show "Dan Smith" does not show anywhere on iPhone). Needless to say, these are actually the contacts that I use most often so I'm hoping to find a solution.
On a related point, it's hard to determine exactly how many contacts are not syncing b/c I can't find anyplace on the iPhone or in iTunes that lists shows info on the number of contacts (so I can't compare to my count in Outlook).
Has anyone else experienced this problem? Are there any known solutions or work-arounds? (I'm hoping to avoid a full export, clean-up, and import to iPhone through the Mac Address Book or similar b/c I'm concerned that in then trying to sync w/ Outlook I'd get duplicates. Also, my contact list has thousands of contacts so it would be very dedious. My current work-around is to still carry my Treo in my briefcase, which is not ideal).
Thanks in advance for any help.

boynsea: Thanks for the input, but isn't the IMAP aspect of Outlook limited to the way one can connect to an Exchange server for e-mail? I've been successful in getting the IMAP connection for e-mail working. Contacts and calendar are designed to sync when physically docked with the computer rather than over-the-air; I know, if something like exchange activesync is ever licensed for iPhone then the calendar can be updated over-the-air, but I suspect that contacts will always be synced only when docked (which is how my Treo was set up).
Anyway, I did test my theory about the "file-as" field by changing a few contacts back to their default display and now they sync just fine. I really don't want to have to do this for all contacts, and can't actually tell how many are involved since I haven't found anyplace that the number of contacts is listed. Also, does anyone know if there is a readily accessible syncronization log that can be checked? That might show those contacts that are rejected.
Thanks.

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