I agree with you re:health care and our inept congress. In terms of entrepreneurship not being right for everyone, I agree. However, the thought experiment was oversimplified a bit.

There are human-required jobs that won't be infinitely scalable. Artist, masseuse, daycare provider, teacher, author, sales, marketer, circus performer, mover, software engineer, owner, landlord, nurse, doctor. The dystopian argument is usually that technology will require less of these jobs. It usually doesn't go as far as saying "none" and that is where the people who aren't cut out for entrepreneurship will land.