Lance,
When migrating from 5.5 to exch 2003, we considered exmerge.exe. This is a MS tool that will 'suck' all the mailboxes and save them as .pst files. The .pst files can then be used to import back to an exchange server OR you can have each outlook client access their .pst file. This would allow you to run exmerge.exe, then shutdown 5.5. Using a backup MX server while you do this, you could then configure your 20 clients to use SME and the .pst file.
Other option would be:
1. setup backup mx server (sme) for your domain.
2. the next day, take 5.5 off the internet. (use exmerge.exe later to export mailboxes if necessary).
3. configure sme with your user accounts. for each user, set email to forward 'user@5.5hostname.smedomain.com' with '5.5hostname' being the sme host name of the 5.5 server...which means exchange uses a dhcp reservation from sme & your set up a local hostname in server manager.
4. when all users are setup on sme to forward email to the internal lan 5.5 server, set your primary mx records to be sme, or put sme on same internet IP 5.5 was on.
5. then, change each user one by one to store email on sme rather than forward it to exchange.
you should test this as this is just my thoughts, but I think it would work.
have fun
ryan