So transparency was arguably still something a true hacker wouldn't waste cycles on.
To your general point, it felt like there was a shift around 2000, when computers needed to be "serious business" and the whimsy of the 80s and 90s was scrubbed out of software.
Honestly, I think we all would have been better off if we'd turned the web to something more approachable for common people (especially if it inspired them to be creators).
Instead, we built a brutalist efficient system where most expression is limited to setting your background.