"For a long time now I've had a registry file to make context menu entries for WinDbg. The entries allow you to select the x86 or x64 debugger. Internally at Microsoft, I have another version of the registry file that contains two more context menu entries for the private symbol server. You can see all 4 options I add internally in this screenshot.
Note, the registry file assumes WinDBG is installed in c:\debuggers_x86 and c:\debuggers (for the x86 and AMD64 debuggers respectively). FYI: The reason you need to install the debugger twice is the lack of architecture agnostic support in some extensions - yes, SOS.DLL I'm looking at you. The multiple entries give you a quick way of jumping between the two architectures.
The level of dev-ness to this just tickles my fancy...