Does their software run in a VM? (perhaps not?, plenty of software has checks to prevent it from running in a VM).

If it does, wouldn't a good recommendation be for anyone who cares about being able to use this software and not lose it in an upgrade to install it into a VM and get its license (within the VM) validated while one can.

This way, one has it backed up in an installed, licensed and runnable state (which will presumably work perpetually for the software one, unless they have checks in the code that force one to reregister regularly for any number of reasons).