I study and write quite a bit of tech history. IMHO from what I've learned over the last few years of this hobby, the primary issue is quite simple. While hardware folks study and learn from the successes and failures of past hardware, software folks do not. People do not regularly pull apart old systems for learning. Typically, software folks build new and every generation of software developers must relearn the same problems.
I've been on some weird path of discovery of the internet and am loving it. Generating my own ambient sounds for work from freesound.org. Finding internet radio stations to stream. Music from bandcamp and https://www.nts.live/. Rediscovering RSS and building my own tooling on top of it. You just have to be deliberate and step away from the convenience of big aggregators and algorithms and there's a whole wonderful world out there.
Not good! I personally use it with my wife but getting people to try it online seems to be very tricky to do. Seems like there's a big trust hurdle to overcome.
https://en.wikipedia.org/wiki/Recutils