Hello
I've developed an Outlook Addin in VS2003 with the COM Addin Shim. It is possible to add some AutoUpdate mechanism like http://www.windowsforms.net/articles/appupdater.aspx or the one from the Enterprise Library. I like to deploy the latest version on the server and let the clients automatically download the latest version.
Thanks
Marco

Outlook addin AutoUpdate
Sameer Simha
You can always roll your own autoupdate mechanism using the standard features of .NET and VS. I have created trickle-down assemblies with an auto-update mechanism as part of the app.
However, in Visual Studio 2005 Tools for Office we have added Outlook add-in supprt. The tools for this support include the use of a deployment manifest so that you can have more flexible deployment and maintenance scenarios as you describe.
I encourage you to learn about VSTO 2005 and use these tools if you can.
Learn about it here:
http://msdn.microsoft.com/office/undertanding/vsto
Regards,
John.