I'm in the same boat with my personal main studio DAW.
It's upgraded/expanded on regular basis...
I don't think about it so much as "dependent upon using the same case".
It's a single machine... no different than if it were a high-performance race car.
The engine might change, be rebuilt, or enhanced... but it's a singular entity.
If I change the case (which is more rare), it's still that single machine (my main studio DAW).
That one Windows license is only installed on a single machine.
If my main studio DAW was rebuilt into two separate physical machines, that's where a new license is necessary.