When it comes to native apps, in the 2000s, this was the common attitude of users. But it's much harder to implement from a business perspective! Both in terms of business models, and in terms of dev time - having a bunch of possibly-incompatible versions lying around is a lot of overhead.

On the web, where most technical users understood this is technically impossible, they were willing to allow businesses to act differently, keep the software always-updated, and charge per usage. And since that's much easier and more lucrative for companies, they all switched to that.

(Now everyone kind of accepts that model, which is why today's Photoshop works via subscription, but the "damage" was done and the web won.)

Devs absolutely do not enjoy backporting bug fixes to 5 different LTS versions of their software and then getting user complaints because there's inevitably an important customer who is six versions back. It's inefficient with expensive dev time and it's better for the business to use that time to create new features.

edanm is correct, a lot of this is historical caused by very loud and angry tech users around the turn of the millennium. Want to know why Chrome won? When telling that story people tend to focus on performance or security, but that's not really it. Chrome won because Larry Page overrode all the internal screaming about silent web-style auto update for desktop apps. Oh boy, a whole lot of people really hated that idea, in fact Google had to develop their own software update engine from scratch to make it happen. Page didn't care. He understood that the ability to release a new version of web apps every week without the user noticing was a huge competitive advantage for the web, IE also updated in the background as part of the OS, and he wanted Google's desktop apps to have that same advantage.

Meanwhile Firefox stuck with the old model of rare releases and letting users choose whether to upgrade or not. It was a disaster. Old Firefoxes constantly annoyed web devs by preventing them from using new features. Security patches got reverse engineered and exploited. Still, Firefox's passionate fanbase loudly rejected the Chrome approach because they felt it took away their control.

Eventually the Mozilla guys accepted that they were wrong, their fans were wrong and Larry Page was correct. But it took years and in that time Chrome had built up a huge reputational advantage.

Businesses don't. Gotta find a way to sell the same shit every year.