Isn't the reason we are freed from barter in daily life is because the government is intimately involved in the financial/banking system, and regulates it and issues money and so on? Maybe we continue to struggle with the internet because it started out unregulated and has never really transcended that because people insist on thinking freedom is best for commerce without appreciating the nuances.
There are alternatives to that. For all of the hype and vaporware of the cryptocurrency movement, the idea of digital-native programmable internet money is a powerful one. I’m personally excited by the idea of involving currency at the protocol level and having it interact naturally over tcp/ip and http. There is an alternative to ads if we can make it work.