[Mark McLeod]

One of the reasons I like to use the Classmate as a test case just to isolate the problem is that it's a common setup for all of us. We know the Classmate connected directly to the cRIO (& running the DS app.) should have the least trouble working together.
It makes it a lot easier for us to suggest where to look next or say "it's a problem with the PC settings", or "the cRIO image looks bad", or "the network is flakey."

For both the laptop and the Classmate, running the DS application at the same time you're timing out on the download will let you use the set of ping statuses to tell exactly what the PC can or can't see when it fails to download.

If the IP's are a little mixed that should become obvious.