I do think there will still be jobs around, but I don't think there will be enough. While in the past more jobs were created by automation there will come a time when most humans will be rendered obsolete in the work place. That is the logical progression. Human labour being minimised as much as possible to increase productivity and profits.
If there is no work for someone to do, how will they have enough money to survive? How will they afford the basics of living without income? This then leads to your point about leisure.
Too much leisure isn't a good thing. People need to work. It isn't always the end product that produces joy, it's the process of making/doing that does. Playing video games all day with no life goals isn't fun in the longterm. That's kind of what I do now, I have far too much free time and it isn't actually fun.
And If you can't work how can you have leisure time? You need money to provide the basics, if you don't have the basics sorted you can't really have leisure.
I also don't like the idea of having most of the control over machines in the hands of the rich. If the rich own the means of production over all goods, what power do we have? They control everything. The disparity between rich and poor will be immense.
Yes people were wrong beforehand, they didn't foresee new jobs being created. Maybe there will always be enough work, maybe it isn't going to be an issue for the next 100 years, but I still think it's worth exploring the possible negative outcomes instead of assuming everything is going to be perfect. We will just have to wait and see.
RE: Doug Casey and I Destroying Commies On Universal Income