Perhaps this is a startup idea for the ambitious types on HN. There are literally 1000's of very successful blogs making some marginal amount of money from ads on their site. Most of these bloggers are not in it for the money and would like a publisher to take care of the business side of things, including the taxes. Perhaps this already exists but I am not aware of it.
Yes, but adding W2 income to your tax forms is pretty easy and insulates you from all the tax and legal implications of running your own blog for a small income. Whereas adding a Schedule C for 1099 income exposes you to all those risks, taxes and complexity. It sounds like the guy who wrote the original blog post didn't really discuss this with his tax and legal advisors because his mistake was easily avoided if he had properly claimed the income.
