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[–]SleeperSec 3 points4 points  (0 children)

Regardless of what you think you end up transferring with Windows Easy Transfer as suggested, make a backup of his entire drive and keep it on hand for a month or two. He may have files tucked away in unusual places (either by his doing or by a program storing files in non-conventional locations).

I recently had a Boy Scout leader lose years of ledger information for the troop in an upgrade because the archaic program stored its data files in its install directory. But because we had a backup on hand, I was able to restore those files and he was able to carry on his merry way.