Actually, this can be achieved little bit easily with .net using "FileSystemWatcher". It monitors the files, created, edited, deleted, and using System.net (I am not sure, here) or "wininet.dll" for uploading/downloading files to the remote server's folder, can be done, easily.
I have done similar kind of thing (but two different projects, 1. for watching file system (.net), 2. transferring files to remote server (vb6.0)) and both can be merged by logical approach.
For transferring files check this link:
and for FileSystemWatcher, you can do it in few steps and few lines of code in vs.net (hardly takes 1 hour or less)
Give a try.
Hope this helps.