What you are describing won't really work, when Windows installs it does a bunch of configuration that is based on your hardware and all that goes into the registry. Some hardware you can switch out from underneath it no problem, and in THEORY you can put a whole new computer under Windows and it'll go through and detect all the changes and work, but in practice I've only ever had this work once. So dumping in the old registry into a new install of Windows will likely result in an unbootable machine.
There's also supposedly software out there that will transfer a program from one computer to another so that it works without having to go through the program's install process (i.e. it transfers over all the necessary files and registry settings), though I've never tried one and don't know how well they work.
Your best bet is to start fresh with a new computer, and then either get legal copies for the software you're using but don't own that you want to move over or look for free substitutes (there's lots of great free software out there).
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Uncertainty is an uncomfortable position.
But certainty is an absurd one.
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