So I'm looking at RSS feeds and notice a person who is having a hard time configuring Outlook over Http on his SBS 2003.

pssst... should I tell him that his information was right under his nose...or I should say.. right under his RWW? If he logs into Remote Web Workplace [your domain/remote]

See that icon in that RWW login screen? It's the exact customized howto to set up Outlook over HTTP on a SBS box.  If you don't want that info, there is also the detailed info at the Magical M&M's site.

Using Outlook via the Internet

If you are using Microsoft® Office Outlook® 2003, you can connect to the computer running Windows® Small Business Server through the Internet using the feature called RPC over HTTP. This means you can remotely access your server e-mail account from the Internet when you are working outside your organization's firewall. You do not need security-related hardware or software (such as smart cards or security tokens), and you do not have to establish a virtual private network (VPN) connection to the server.

Comparing RPC over HTTP and Outlook Web Access

When using RPC over HTTP to access your mailbox, you get the full functionality of Outlook 2003. For example, you can work offline, use Microsoft Office Word 2003 as your e-mail editor, and easily organize your mailbox.