I appreciate the use of a cobbler or ‘shoe maker’ as your example! What intrigues me is this question space that includes the idea of basic income but also includes the concepts of the circulation and role of money and the transactional processes. If we have an entity that can produce shoes without humans involved (or just a handful in number) how do the large number of humans, who want and need shoes, interact to get the shoes? Who owns the shoe making machine, do humans still trade with the machine or are we allocated shoes — markets or commands? Are humans segmented into groups? Those in a system that transact with the machine and end up with thousands of pairs of shoes (think Imelda http://www.abc.net.au/news/2016-10-02/imelda-marcos-shoe-museum:-the-excess-of-a-regime/7877098 ), as distinct from what I would expect would be a vast number of down-at-heel, precariously existing humans who may revert to crafting their own shoes from the waste streams of the machine.
There are these dystopic visions of the future that extrapolate from our present trends but there are other options — technology is offering us a choice to create a world where we (10 billion inhabitants eventually) can all work: to produce necessary and useful goods and services; to enable us to use and perfect our gifts and skills; and to serve, and collaborate with, other people, so as to “liberate ourselves from our inborn egocentricity.” (E.F. Schumacher, Good Work). Perhaps our work, our useful service, is to steer towards this.