Skip is trying to do a clean install of Windows 10, but it won't take his password, even though he reset it. He talked to Microsoft and the rep said he'd need a new product key. Leo says that's nonsense. Here's how it works, and it's been verified by Paul Thurrot at Thurrott.com. The upgrade is associated to the machine, not the serial number, nor the account. It's the machine.
So the clean install should work. Skip should follow the step by step instructions in the link above and it should get him through it. Another option is to go into Recovery and choose the 'wipe everything and start over' option.