The $19.99 upgrade price is for ANY registered Cakewalk user, so he would be qualified for the upgrade.
I HIGHLY recommend that you (the original poster) take advantage of the fabulous sale price for the basic version of X3. It will most DEFINITELY run in Windows 7.
I suggest you launch the X3 installer with the explicit Run As Administrator (not just from an Admin user), and also, once it is installed, download and install the latest X3 maintenance, which is X3e. (it is cumulative, so you don't have to install each of the other maintenance updates, such as x3b, c, or d).
Best of luck with all,
Bob Bone