So far I haven’t had any upgrade related problems with the two systems of mine that I upgraded to Windows 10. I waited until the last month of being able to update for free on each of them.
I really only use 2 systems running Windows on a regular basis. One was a notebook that had been running Windows 7 Professional and whose use has really been limited since I got a 9 inch Android based tablet and Bluetooth connected keyboard. I started having problems with Windows Update on that system not completing, and made the decision to apply the free update to Windows 10 to it. That took a while to get the download and installation to complete, but once it did, everything seems to be working fine on that system. I did have to uninstall a lot of the OEM provided security software I was using on it, as it was not supported under this newer version of Windows.
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The second system I updated on the very last possible day to upgrade for free, was my main desktop which I use for web browsing and PC gaming. It had been running Windows 8.1 Professional and after the upgrade is now running Windows 10 Pro. It’s upgrade was pretty straight forward and took less time to complete. I haven’t run into any issues with the Steam distributed games and the Nvidia applications and drivers I use on that system. I declined a lot of the options that would have changed default applications and added new Microsoft stuff, so my user experience really hasn’t changed that much, and I like it that way.