I upgraded my laptop – more memory, and a larger hard drive. Not a difficult task, the longest piece of the job was resizing the partitions after dd’ing the smaller disk onto the larger one. Windows worked without a blink. It didn’t consider the upgrade reactivation-worthy (which is good).
Acrobat was a different kettle of fish – I needed to activate it again. I’m pretty much convinced that the activation data is based on the hard drive – probable the model and capacity. The tell-tale sign for this is that it refuses to work when you are running partition magic. As partition magic’s documentation is in PDF, this makes things quite silly.
This is ‘slightly’ covered on the activation FAQ, which mentions that if you low-level format your hard drive you’ll lose the activation information.