Question 1:
I know that Bob Black spoke a fair amount about “turning work into play” (which in hindsight is eerily similar to the “gamification” craze, but I digress), but how would the kinds of things that are highly unlikely to appeal to anyone but would remain necessary be dealt with (assuming that there are no sudden breakthroughs in automation that would make it unnecessary for humans to engage in it, which I doubt is likely to happen this century)?
Specifically, this would be garbage disposal, toilet cleaning (or latrine pit emptying), work with corpses, and so on. Fourier mentioned the idea of having small children who have yet to develop an aversion to such things do those tasks, but that seems like it would both put the children at unnecessary risk and cause other issues like scattering garbage all over rather than throwing it away. The best option to me appears to have people volunteer or take turns to do it and reward them for doing so (punishment seems unnecessary as a motivator, as the result of not doing those tasks would be its own punishment).
Question 2:
How will tasks that require extensive training to do effectively be done in a post-work world without compromising its quality? The STEM fields are certainly the most obvious ones in this category, but I could imagine humbler but still complex tasks like electrical wiring or vehicle repairs to require a degree of specialization that would bar anyone from simply dabbling in it unless the people they would serve were willing to take unnecessary risks.
I guess one could argue that the need for training and general competence would separate those who genuinely want to do those tasks from those who don't, but that doesn't seem to allow much room for the “Golden Age of the dilettante” Black advocated for.