I did an upgrade of four computers from Win 7 x64 Pro to Win 10 x64 Pro (for free back when). I clean installed two computer with Win 10. One of which was an upgraded computer that had a C:\ hard drive crash after a power failure (would not boot). That was my DAW (?). If you know anything about my DAW it has miles and miles of plugs and libraries. It truly took nearly two weeks installing everything but it also allowed me to discard two DAW product I got as crossgrades in the dark days after SONAR's development was stopped (MIxcraft & Samplitube).
Ummmmm, the Cakewalk Command Center did just that. It had the ability to roll back to any version you wanted. I even did it a few times just to be sure I wasn't 'drunk at the time' something went nutzo.