To my knowledge, DropBox (and the like) uses the Windows service (or daemon on the Linux / Mac side) to monitor the file system. Creating one in .Net is very simple, and this script is usually an example tutorial for Windows services. I believe that doing a similar thing in C ++ would be pretty straight forward.
Here is a link to a simple .Net tutorial on how to create a service on Windows. All you need to do for your solution is to add monitor logic to the Timer.Tick () event.
http://www.developer.com/net/csharp/article.php/2173801
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