Most things can just be copied from one to the other, e.g. macOS applications are supposed to be drag/drop installs. All files can be copied from one to another without problems.
But anything requiring a 3rd-party driver will be an exception, and that includes the software for a hardware key (and possibly a software key too). Generally you can find an installer just for the driver (on either OS version), so it shouldn't be a problem.
I use Parallels Desktop for running previous OS versions, so I don't need to reboot to run older versions. It works well.
Ralph Wessel BArch
Software Engineer Speckle Systems