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I bought a new dev laptop and I am wanting to transfer the complete environment (files, programs, OS everything) to the new computer, completely wiping out the default layout of the new computer's hard drive in the process and replacing it with everything from the old system.

Both systems are running Win7 pro. I don't have enough space on the network for the image, but I do have a 300GB USB Hard Disk (a HP HD3000s Personal Media Drive).

I managed to use the Backup app in Control Panel to put a new system image on this drive, but when I then switch over to the new computer, plug in the USB cable to the drive, and reboot the computer to the Windows Recovery Environment (WinRE) and then it won't let me pick the USB hard drive as a source for the restore.

Is there something I'm doing wrong?
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I don't completely understand what you want to do. Sounds to me like you want to move your running system to new hardware, so that you need not re-install programs and make your preferred settings. Correct?
The new PC may have hardware different from the old PC, and drivers may not be installed. Go to device manager and look out for devices which are not properly installed, and let Windows try to install drivers from the Internet (or from the board driver CD if you have one). If that doesn't help, try a repair installation from your W7 DVD. I cannot give you details but there should be instructions on the internet.
Are you aware that you must re-activate Windows on the new PC? So better have your license code at hand.
 
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