OotD crashes on startup. What's wrong?

A symptom of this is the following error message on startup:

Error HRESULT E_FAIL has been returned from a call to a COM component
or

Unable to cast COM object of type 'Microsoft.Office.Interop.Outlook.ApplicationClass' to interface type 'Microsoft.Office.Interop.Outlook._Application'
There is no one definitive answer for this. In most cases it is caused by an incorrect or partially corrupt installation of Microsoft Office. Doing a complete uninstall and reinstall of Office usually fixes it.

If uninstalling did not work, you can also try the Microsoft Office Cleanup Tool to wipe any traces of Office before reinstalling.

If you get this error on startup:

Show Desktop in Windows Vista and Windows 7 hides Outlook on the Desktop as well. How can I fix this?

Unfortunately, there is no way to fix this.  Microsoft decided to strip this functionality from Windows Vista and above.  However, there is a trick that still works:

Hold the "Windows Key" and press M to minimize all windows.  It will minimize everything except Outlook on the Desktop, essentially achieving the same effect as Show Desktop.  "Windows Key" + Shift + M will restore your minimized windows.