Outlook / Exchange 2003, autoarchive not working

I have a client running SBS2003 and outlook 2003.  For everyone except the boss, all is running smoothly.  Everyone manages their email and everyone except the boss maintains there mailbox around 2-3Gb.  While that's still pretty large size, there are no performance issues...for them.  Now we come to the "boss" and his 14GB worth of email going back several years.  When he does any kind of search it can bring the server to its knees until done.  And as most "users" he'll keep clicking and clicking until things get ugly.

I decided to make his outlook run in cached mode to make the bulk of the heavy lifting occur on his machine, but he still has performance issues.  I then thought about trying to archive his mail to an archive pst, since his profile is roaming and that would also be backed up each day.  When I attempt to run autoarchive nothing happens.  Perhaps I'm missing something?  Does anyone have experience with exchange server and autoarchive or other performance tuning.

The data store runs it's online defrag successfully each night and backups are also run nightly.  Other than his issues with email, everything is and has been humming along nicely, but he refuses to delete mail and when he does, thousands of messages sit in the deleted folder...just in case.  Realizing that this is as much a use issue as anything, I'm trying to automate what I can to better his performance.  Any feedback/suggestions would be appreciated.