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Capitalism has been automating for the past two centuries.
Only for the principal sake of increasing profits -- any benefits from technology produced, for the consumer and/or others, are sheerly incidental to the profit motive itself.
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However it has a rationale and a justification for determining "unnecessary pain and trouble."
Translation in this context: Costs to capital.
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At what costs for as much free time as possible?
Well, since in a *collectivized* context 'costs' would be mass-efforts-in-common, it would be up to the world's population as a whole to decide the exact 'cost' of free time (non-productivity), to society as a whole.
Those individualistically putting in more labor than the norm would be cheating themselves, in relation to the norm, which I'm sure no one else would mind. Those individualistically putting in *less* labor than the norm would be a *political concern* to the collective political economy, and would have to be addressed somehow.
You're implicitly noting that there's an inherent trade-off between free time and material productivity, so that's always the reality for everyone, no matter what the socio-political context.
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How do you know if you have reached these objectives?
As in past exchanges, Baseball, I am unable to address the specifics of a hypothetical since that would be an extrapolation within an extrapolation, or purely imaginary. The general answer is that the denizens of such a post-capitalist political economy would be self-empowered by that point to work it out as they see fit.