I have a pet theory that this is connected to stagnating wages over the last 40 years or so. If consumers had more disposable income they would be more willing to pay for software.
The shoes cost 50$, so paying him $30 to repair them was an acceptable purchase.
Now the shoes cost $100, but nobody can afford to spend even the original $30 to repair them because they have no money. Also the shoe repair man can't run a business anymore because the shoes are borderline unrepairable, such that even if you replace the sole or any other part, the rest of the shoe is just as worn out and useless.
Most engineering effort the past 30 years has been in making things out of materials that are just barely adequate. "It takes an engineer to put together a bridge that just barely stays up" also means it takes a department of engineers to shave one cent off the BOM of these shoes that also happens to make them last half as long.
Which again is a "feature" of the design from the company's perspective.
"Now introducing ads to your paid service. Dont like ads? You're in luck, We just introduced ad free tiers! Just purchase produkt++ for an additional $19.99 a month"
Also because corporate software (ie. anything popular) had a tendency to start complicating the licensing terms. Sorry, that feature is not available in the Home edition. And nowadays you can't even buy a lot of software, you have to pay a recurring subscription.
It's the old Gabe Newell line about piracy being a service problem. If you make paying for something so much harder than not paying for it people will either pirate it or just not use it at all.