> all you could use was tech from 2000 and before you would have a pretty stable stack that just worked

The improvements made during the late 2000s and 2010s mostly had to do with making the functionality of these technologies accessible to non-technical users. I was younger and probably more mentally agile back then, but I remember the first iTouch I ever bought being very intuitive to use; you could usually intimate what you wanted to do without even looking it up. I got so accustomed to this intuitiveness (Windows Vista being an unhappy interruption in those series of memories) that by the time Windows 8 rolled around I was completely taken aback by how bad it was.

I mentioned in another comment that these productivity apps only really see a positive net expected value at the enterprise level, where they aren’t primarily used for efficiency but as coordination mechanisms and institutional memory. Individual users can only really hope to take advantage of them if they are intuitive to use.

From what I’ve observed, most of these UX failures are not the result of a lack of technical aptitude, nor an issue of cost, but of failures in institutional coordination (principal-agent problems and things like that) or the market simply being cornered; both follow the general trend of consolidation in the tech industry. The companies that are making most of our software are huge and they lack the competition to incentivize them to improve.