Hello,
I've created systems similar to what you are describing, in the past.
I've been using C# since 2008 (.NET since 2003) and have written many, many, applications - both desktop and web based. I'm just trying to get my foot in the door, here on Freelancer. So, if you were to select me for the project I would write you a kick-ass updating system just for the review. I can even do the server-side of things, providing you are using ASP.NET. I have a private server to develop and test on.
Hope to hear from you soon!
Best regards,
Scott Michaels