Outlook 2003 throws "Operation could not be completed error" when using Sent To: Mail Recipient

I have a client who is using Office Pro 2003 who is experiencing an odd problem with Outlook:

When using the Send To: Mail Recipient to attach a file to an e-mail (Word or PDF), if he types in the "To:" field, this error is generated: "Operation could not be completed"

Outlook then locks up and appears to use a steadily increasing amount of memory until killed.

If he uses the Address book to choose the recipient address, no error is thrown.
If he creates a new e-mail in Outlook and attaches the file, no error is thrown.

Of course we could have him use the Address book as a work around, but he sends a large number of attachments to clients and the error does not allow him to type in e-mail addresses of new contacts not in his address book.   We could have him create a new e-mail for attachments from Outlook, but this greatly slows his work flow and interferes with his ability to send from documents pulled from Time Matters which he uses as a document tracking system.

We have tried a repair install of Office, we have run Scanpst on his Outlook.pst.  We have  tested with all Outlook addins disabled.

It is probably worth noting that he uses Time Matters, with an Outlook plugin to sync e-mail communication with Time Matters.  He is experiencing problems with this plug in causing Outlook to freeze in a similar manner.  However, as noted above, disabling the TM plugin does not resolve the issue.

Any thoughts?
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