just to add, I have actually done this before, but I have a full version of Visual Studio, not the express version. Basically, my own applications check the webservice for new updates, the webservice gets the version of the file that the caller has, and checks on the server for latest versions and sends it across to the client, but in order to make WebServices, you need ASP.NET/full version of Visual Studio.
I'm unsure, you could probably use clickonce or something I'm not really an expert in that area
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