Okay well the key problem your running into is the Post-Vista security system prevents any sort of method your suggesting, due to the very things your post initially started with and what I made points to, and certainly can't do as your asking especially if they are from OEM systems (Dell, HP, etc.) as that prevents the OS from being used in ANY OTHER HARDWARE configuration.
So to step back and look at what you got here, I would tell you the following:
If your trying to rescue data, then simply run Windows Easy Transfer on the Vista and 7 builds. 8/8.1 prevents that from occuring and you can only synchronize the data by making sure the data (say documents, pictures, etc.) is selected under your ONEDRIVE (the little cloud icon in the tray, right click and select the folders, and there is several Googled tips on how to backup your data to OneDrive). When you reinstall Windows 8, then upgrade to 8.1 (Windows store) then apply the Update to the Update (Windows 8.1Update) during this the cloud will synch automatically all your data back down based on that email account you setup for it.
Next I would tell your son, that Vista can't be reinstalled and it isn't supported (true) anymore everyone is on Windows 8, which there is a simple menu add on to get the 'orb' look and feel to it (again simple Google). Windows 7 is the same as Vista, which shouldn't push your son too far from freaking out, but the problem now (as a Consumer) is it isn't supported either. All Windows 7 / 8 editions will be eligible for a free upgrade to Windows 10 after April 15 per Microsoft (that is when the Consumer Preview edition expires and the released version should be implemented). So it is quite academic about having multiple versions.
Again the main issues is licensing, each edition, is ONLY viable with the system they came with. If you want to keep a working HD for a computer with a copy of Windows on it, you need to purchase a new license copy, whcih is Windows 8. In all cases you will have to reinstall the OS and apps, there is no way around it EXCEPT if you use a BIT LEVEL Backup solution. Someone suggested Malciem I believe it is called, but one of the Mods tested it and it failed bad with the image and restore. So as I mentioned the way to go now is the method I outlined. Sorry.