You can work around this in the event that your commercial software provides a consistent interface for the license key stuff; e.g. via the CLI, a key file (ideally plain text) on-disk, or some scriptable interface.

Then you can store this info in separate key management software (e.g. Unix pass for your local machine) at which point bootstrapping your system could be done relatively automatically.

EDIT: I should add that this is my view of how things should work in the-world-as-it-ought-to-be, which isn’t necessarily the same as the-world-that-we-live-in.