This is an interesting scenario, since it seems that you are doing all this on one computer (both on the client and on the server). I answer a vague original question and would like to receive additional data in order to fully answer this question.
FTP upload itself is not supported by Silverlight, but the concept of file upload is through an HTTP data stream.
If you want to download HTTP from the client machine to the server: you can use the OpenFileDialog control in Silverlight 2 and 3 to read this data, then use WebClient to download it.
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