Neither of you has gotten the point. A billion dollar company understands market trends far better that smaller ISV. There's nigh 7 billion people on the planet. The trend is clearly moving towards more affordable software that can be sold globally. WWDC again banged the "localize your app and go global" mantra.
Paid upgrades are messy. I just bought Hypes Tumult 2. They put it on sale for everyone and it sufficed for an upgrade. I'm not going to complain about new users getting the same price. The belief that I, as a former user, should always have a cheaper price than new users is entitlement behavior.
Paid Upgrades stink. They force developers to create a cutoff date. People outside those dates don't get the upgrade pricing which causes rifts.
Apple knows what they're doing here folks. Paid upgrades buttressing overpriced software is old ideology. Come into the 21st century.
And what's this crap about "I always buy locally from the vendor" That's stupid. I've got four Macs and about to buy more. I'm not going back to tracking serial numbers so that I can save a vendor %30. My allegiance is to my family. If a company makes my life easier then i'll pay a respectable price but i'm not into charity cases within the tech sector.
The dollarness of a company has little to do with what they understand. There are plenty of examples of "billion dollar" companies completely misunderstanding markets. Sometimes even because they have gotten so big they've lost touch with what's going on.
What is messy about paid upgrades (in general)? You haven't said anything concrete here or refuted anything.
Why do paid upgrades stink? As for a cutoff date causing rifts, welcome to the way economies have been for centuries. How is this different from any other product going on sale? Those who bought it the day before paid more, those who wait until after the sale paid more? The rest of us seem to be able to get over it.
If a particular piece of software is overpriced don't buy it. Period. Upgrades or not, free or not. In an efficient economy things will find their market price. It's not hurting you at all to allow every vendor to decide their pricing strategy.