I pay for a connection and a device. I don't pay for an advertising subsidy. If you choose to use advertising as a capital model for your business in a market so easily destroyed by technology then that by definition is a shitty business model due to the massive risk of a technological shift destroying your only income. Not only that, the consumers merely tolerate your model, not engage it. It is a plague upon them most of the time.
The only way this model works is if you provide a device which consumes advertising. That in itself is being eroded as well due to the number of services which offer utility without advertising even on the advertiser's territory.
Content isn't worth much on its own which is the problem. Authors rarely get paid anything significant from publishing; same with content driven advertising. I don't see how you're going to milk it in a decaying market.
The web will shrink, content will have to stand alone and be free of advertising ties and you'll have to put some cash down for services. Back to 1995 again.
I fully expect these dying markets to throw a few turds yet however. That will merely bury them deeper.