Regarding 3), I would guess that re-education always seems more difficult initially and the hurdles are reduced overtime. It must seem have seemed impossible that a farmer would be able to operate a machine in a factory, initially. Also, there are always new people entering the work force that are being educated under the new paradigm.
These days it appears that a lot of effort and innovation is focused on creating services that encourage the 'democratization of software development' which allows traditionally non-technical people to more easily create software and online services. Think Heroku, dotCloud, Twilio, etc. This innovation will continue to lower the barriers of entry into the new economy and allow normals to build.
When you hear people say 'this time it's different' it almost never is.
To be fair, assuming you are a developer or an entrepreneur, your basic job description could be boiled down to either constant self re-education (coding skills transferred to platforms that did not exist when you started) or adaptability.
I feel, being in this field that requires constant learning (there are some jobs that require only static ability, e.g. COBOL mainframe), that we have a jaded view of what it takes to learn something new. Going from accounting to HR is a big leap, completely different domain (not like picking up iOS after doing server-side Java)
These days it appears that a lot of effort and innovation is focused on creating services that encourage the 'democratization of software development' which allows traditionally non-technical people to more easily create software and online services. Think Heroku, dotCloud, Twilio, etc. This innovation will continue to lower the barriers of entry into the new economy and allow normals to build.
When you hear people say 'this time it's different' it almost never is.