If you had a bunch of machines that did EVERYTHING for you, including maintaining the machines, you wouldn't have a job, but you'd be living like a king, or a god. Not having to work is an unmitigated blessing, not a curse.
This would only be true if you owned these machines, or enough shares in them to get income from them. If not, things could be very bad for you.
Just because a worker is less productive than a machine doesn't mean he is out of work. All it means is that his wage is lower than the machine's "wage".
And if a machine can operate on the equivalent of $10 per day but be 10x more productive than you, then your wage would be driven down to $1 per day. Just because you could make some small wage doesn't mean you'd be able to live off it.
And by the way, forget about the "Tech Elite". They will be the first to suffer from falling wages, since pure knowledge jobs are the easiest to replace with software.
Software development jobs will be some of the last to be automated, since they are very mentally difficult. I agree that software replacing skilled programmers will likely happen before software can replace Louis C.K, but both of those jobs are still be among the very last to be automated. Think about all the other office jobs out there: people working in payroll, handling purchase orders, etc. All these jobs are much easier to automate than software development.