There were a lot of things that sucked about tech in that era! It was literally when pets.com ads blanketed the airwaves. (edited to add: And more specifically, I think the exact time the OP is describing was already too far down its current path of ubiquitous social media (remember Friendster, MySpace, LiveJournal, AO3, etc.?) and omnipresent commercial surveillance. The fork point to avoid those fates was probably a decade earlier.)
But I think we can all agree that it is absolutely when music peaked, and pop culture has just gone downhill since then. :)