This is how I back my files up
I export the registry settings from my current Outlook profiles subkey in HKEY_CURRENT_USER\Software\Microsoft\Windows NT\CurrentVersion\Windows Messaging Subsystem\Profiles
And copy the following folders from your current user profile directories. (this assumes your PST files are in the default Microsoft locations).
%userprofile%\Application Data\Microsoft\Outlook and %userprofile%\Local Settings\Application Data\Microsoft\Outlook to the equivalent directories for your user on the new machine. Import the registry file on the new machine. Install (if necessary) and I launch Outlook on the new machine and I was good to go.