I don't get it. It used to be software licenses were being sold for like $10 or $20 dollars. Now $.99 a month is somehow more palatable than $20 for life? I don't believe it. I think perhaps organizations got too large in their bureaucracy. Times were probably leaner for the business folk when software were sold for $10 and $20 or even $120 dollars for Adobe products.

All that being said, it stands to reason you could structure your business to be lean enough to ask for $10 or $20 or $120 licenses again, because it worked fine a decade ago, and nothing significantly changed to make it not work now other than all the sexier corporate real estate these companies have invested into across the US and expanding administrations.

You could take a share of that profit from license sales after paying your immediate overhead to set up some sort of trust that can pay out maintainers for that software long into the future. It can even be structured to outlast the development company if done correctly.