Is there a utility for Windows that allows you to test different aspects of file transfer operations across a Lan or a Wan.
Example...
How long does it take to move a file of a known size (500 MB or 1 GB) from Server A (on site) to Server B (on site) or to Server C (off site-Satellite location)?
D-ITG will allow you to test many aspects of your links. It does not necessarily allow you transfer a file directly, but it allows you to control almost all aspects of the transmission of data across the wire. If all you are interested in is bulk transfer time (and not all the nitty-gritty details) you could just use a basic FTP application and time the transfer.
Probably nothing you've not already figured out. You could get some coarse grain metrics using a batch file to coordinate:
Copy file might just be initiating a file copy between two nodes on the LAN, or it might initiate a FTP copy between two nodes on the WAN.
Monitoring could be as basic as writing the current time to output or file, or it could be as complex as adding performance counter metrics from the network adapter on the two machines.
A commercial WAN emulator would also give you the information your looking for. I've used the Shunra Appliance successfully in the past. Its pretty expensive, so I'd really only recommend it if critical business success is riding on understanding how application behavior could change based on network conditions and is something you could incorporate into regular testing activities.