have you ever consider using a Citrix solution for running the emulator? This is, in my mind, the answer to your problems...
anyway, if she is getting a connection in the VPN, then running the program, if it's timing out, it's a problem on your end. The connection through the VPN makes her machine active on your network, so it's getting there. The program could have an issue with several things, but I think it's problably something to do with the amount of time it's taking for the application to get a response. See if you can configure the interface for running a longer timeout session and see what that does.