You should read up, or better yet talk to people, about retiring. So many people struggle with retirement. It is hard to find a new purpose for life after a big chunk of who you were is gone. Most people I have met tend to take up volunteer work, charity, running some hobby project or some other busywork (I know more than one person who retired into playing MMORPGs fulltime). Most hackers retire into one project or another.

If you have never been without a job, you have no idea. You are hardwired to seek social acceptance and reward and a job is the main way society says you should achieve that.

2) The overall quality of life of people is determined by the application of time and labor saving devices, as well as by technical enhancements to lifestyle and health. There is no higher improvement of quality of life than low infant mortality and longer lifespans. All of these things are delivered by a society that embraces specialisation as a way of increasing productivity by everyone.

Sure, you'll get no argument from me that pointless consumerism backed up by debt-based spending is not the path forwards, but that is an entirely different proposition to stopping working altogether. Only the committed hobo will get satisfaction from a life like that.