You're massively overthinking this. Get yourself a decent installer snapshot diff tool like Total Uninstall, run it each time you set up a new app, and just u

You're massively overthinking this. Get yourself a decent installer snapshot diff tool like Total Uninstall, run it each time you set up a new app, and just use the machine. The ability to thoroughly remove software you discover was bloaty will let you run this thing cleanly until well after the version of Windows is no longer supported. (And no, don't be so naive to think Windows X will really be the last version ever published and you'll just auto update forever, ain't gonna happen).