[cmh0114]

I can't get the video to run on my computer, so sorry if I mention something that you're already doing...

Make sure you have the IP addresses set up correctly and that there are no IP conflicts on your network. If you're in an area with a wireless network, disable your laptop's wireless adapter to avoid interference. Like sunit said, make sure your firewall is disabled - you shouldn't be connected to the Internet at this point anyways.
Once that's done, make sure you set the correct .out file for your project.

I'm not sure what the first error is caused by, but the second error sounds like your wireless bridge on your bot either isn't booting correctly or isn't booting at all. If you have another bridge, test that to see if it works. You should also try connecting with the Classmate, just to make sure it's not some obscure setting on your PC. And try lengthening the timeout period to some crazy long time so that you absolutely know that it's not connecting, as opposed to it starting to connect but then timing out.