Maybe you're too young to remember the kind of vibe and optimism that people rode in the 90s.

Felt like everything was going to be better, like we humans were going to be better. More peace, no apartheid, no Soviet union, removing borders between countries in Europe, tech felt like a way to connect us.

In fact, I invite you to re read your entire post. You post achievements in conveniences as major milestones for human progress, but...people have never read as little as they do today, never went to so few concerts as today, or the movies and the average adult in US spends less than 4 hours socializing (including both family and friends) per week, that's less than half the quote of the 90s which was already less but not as significantly.

Social dislocation, a loneliness epidemic, the breakdown of civil society and of trust in the media, gambling unleashed in everyone's pockets, billions of dollars spent trying to get you addicted to scrolling on your phone... Yes, it's worth bemoaning that.

Maybe I'm missing some sarcasm here, but it would be worth asking what the consequences of this situation are for the people who actually make all the music/books/films you get to consume for a "comically small amount of money".

I Live in a Techno-Dystopian Surveillance Nightmare and All I Got Was This Shitty MP3 Player

You're arguing convenience for things you could already do through a library over the huge amount of negatives that has come with the Internet: crime, espionage, hacking, emotional manipulation, spread of propaganda and disinformation, social media, legalized data stealing, destruction and abuse of copyright, centralization of information flow, etc.