The app store is 3.5 years old, not one, and has been so successful that the original poster mentioned that "practically everyone buying software does it that way."

Nobody is suggesting that the app store should sell software the way that Oracle does. In fact, the point was exactly the opposite: that there's a reason that software is sold differently in different price ranges. And the reason for that is that customers expect it that way.

Some vendors may be bold enough to tell their customers to get bent and that if they want to buy their software they have to do it the way the vendor tells them to. Most of them will go out of business as a result. Ignoring your customers is rarely a good way to sell to them.

What usually happens is that we see segmentation that's pretty close to what's described in the original post: non-enterprise software is sold via a transparent process and aims for scale by selling to small and medium sized customers. The transparency is a business requirement: you can't invest $10000 of a salesperson's salary into selling something for $99/month. Enterprise sales run with enterprise processes because enterprise customers demand that it work that way. The point here is that these processes aren't ordained by vendors, but by customers, and the economics around the deal size.

For vendors that are focused on the enterprise, usually, they're not super concerned about losing the folks on the low end (just like SMB product sales aren't worried about losing enterprise customers). Usually the folks that are frustrated are because they're in one category and trying to buy from the other.