Well in the 90s and early 2000s you really could make money as a small local artist in a niche genre. Think of the people who could cut 500 white labels of their new UK Garage tune and reasonably expect to sell them from the back of their car and turn a decent profit on it.

The ability to be a small time artist, musician, etc and live in the 90s depended on the combined effects of technology and local organisations. You could play on pirate radio, you could go on benefits without too much hassle, you could stay at a squat, you could make your own physical products cheaply, there were lots of venues to play at, you could sell your products for cash and keep it.

The internet makes the distribution of music files cheap and easy, but combined with the increased technologising of society, the rest of the infrastructure that made the 90s a time where culture felt like it was on an e-rush with everyone else have fallen apart.

Can we actually separate distribution from sharing?

I notice that all the advertising examples you listed are about spending time and not money, I'm wondering if there's something there?