There is also the option by well written professional wherer the startergy is to grab as much market share as they can by allowing the proliferation of their product to lockup market/mindshare and rleaget the $ enforcement for later - successfully used by MSWindows for the longest time and Photoshop .

Conversly i remenber Maya or Autodesk used to have a bounty program for whoever would turn in people using unlicensed/cracked versions of their product.Meanwhile Blender (from a commercial past) kept their free nature and have connsistently grown in popularity and quality without any such overtures.

Of course nowadays with Saas everything get segmented into wierd verticals and revenue upsells are across the board with the first hit usually also being free.

As a business, dealing with Microsoft and Oracle is not a clean transactional sale.

They turned into legal-service-firms along the way, and stopped real software development/risk at some point in 2004.

These firms have been selling the same product for decades. Yet once they get their hooks into a business, few survive the incurred variable costs of the 3000lb mosquito. =3