Here is what looks like a very handy piece of software for your troubleshooting tool kit whether you provide tech support formally, take care of your own machines or help friends out.
The Microsoft Outlook Configuration Analyzer Tool (OCAT) provides you a means to check out an Outlook profile for common configuration issues that could create problems in Microsoft Outlook.
The Outlook Configuration Analyzer Tool provides a detailed report of your current Outlook profile. This report includes many parameters about your profile, and it highlights any known problems that are found in your profile. For any problems that are listed in the report, you are provided a link to a Microsoft Knowledge Base (KB) article that describes a possible fix for the problem.
The download includes a 28 page guide on how to download, install, use the software and interpret the reports you get from the OCAT.
According to the download page this software only works with Outlook 2007 and 2010.