For HD testing none better. SpinRite
https://www.grc.com/sr/spinrite.htm
As for Windows I have upgraded in place 2 Win 7 Pro machines with no problems. I have a friend that did 4 machines in place that had win 7 Pro and Home on them No problems.
On my 2 machines I let Win 10 do its updates all the time and have not had a problem.