Software based services businesses exist today that could be feasibly run by one person (or a handful of people which is really not too much different for the purposes here). What you describe has already happened to some extent. It has been causing problems and that will continue and possibly get worse.

Your post is rambling so there's a lot to address.

On the final question, a stateless society is not feasible anytime soon nor particularly desirable. Some use of leadership (soft power), and positive and negative incentives will at least occasionally be compelling to address problems humanity faces. A money-less society is more achievable and can be imagined in a number of ways. One example is a reputation based rewards system. There's a book "Down and Out in the Magic Kingdom" that imagines a society where the currency is based on reputation in a transparent way. I don't think this is necessarily a better system than our kind of currency, but with imagination we can discover there are at least some other options to consider.