Indie shareware vendors predate "software companies with lots of capital" by decades. The big fishes seldom innovate anything.

Shareware is not SaaS/subscription-based software. That's the bad part, not "try before you buy".

Not really. There has always been shareware, aka trial demos.

Those were only utilities and games, not your office software.

Fair, but I don't think this negates the overall point, that people actually paid for software, and it was usually a one-time fee (often with the choice to pay again later for upgrades, or continue to use the old version forever). The "try before you buy" and expiring nature of shareware was nearly always known at the time of download, before investing time in using the software.

No, the users definitely play a role here.

Remember how it became a meme to just pirate Adobe software because they were so bloody expensive? Well Adobe wants their earnings, regardless if their desire is justified, so Adobe and the rest of the industry changed gears to a model that greatly inhibits piracy and, at least in theory, reduces the upfront cost a customer has to pay in exchange for a higher cost over time.

Adobe is basically a monopoly and it is well documented that they allowed piracy because it meant that the pirates would become dependent on their tools.

Doesn’t matter how you edited a photo technically, it is still photoshopped.

Yup, same with Microsoft - they won the desktop OS and office productivity markets thanks, in big part, to their tacit approval of individual-level pirating of Windows and Office.