[Crinus]

> in the past licensing wasn't really compatible with these kinds of scenarios, and you'd often have to purchase the software 5 times.

That is only because of greed. During the 80s and 90s, Borland for example had a "no-nonsense license agreement" that told you to treat the software as a book: make as many copies as you want, have as many users as you want and even resell it as long as - like a book - only one person at a time is using it.

They did change it at some point in the 2000s, probably around the time when they stopped selling Delphi for $99 as the cheapest option, introduced online DRM and prices skyrocketed to the thousands.