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We upgraded all of our machines without issue -- except one. It was an HP Pavillion Desktop that shipped originally with Windows 7, then was digitally upgraded to 8 then to 8.1 (BUT, on that machine, we had also purchased Windows Media Player add-on). The only difference between that machine and every other one we upgraded without error is that it was an HP machine and it had Windows Media Center (the premium add-on) installed.
What I did on that machine was buy an SSD drive, then an old OEM version of Windows 7, and installed windows 7 from scratch, then upgraded to windows 10 without issue. Then I simply plugged in the old original hard drive, copied over all of my docs and pics and such, then wiped it and made it the drive for storing all of the programs and libraries... keeping the SSD clean for the OS.
Try that, the entire cost was less than $150 and it basically gave us a much improved system without all of the HP bootup crap on it. I should have done that the day I bought the machine.
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NSFW
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