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Suppose I said that if you use your optimum free weight workout you must cut it by a third. Across the board. And stop two reps short of failure when you otherwise would not have. Would you still surpass the results you would get from your optimum machine workout?

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Yes. (A guess.)

Part of this hinges on how one both defines and verifies/measures superior results.

Likewise the idea of devising an optimum program and then reducing the volume and/or intensity 1/3 is much less coherent than I suspect you imagine it.

You wave your hands and attempt to assume away things that diverge from however/wherever you want to lead discussion and it is folly. It mattered that Socrates was the guy leading Socratic dialogue.

If one values hypertrophy over all else versus what it is in vogue to call functional strength then I suspect the answer will be different.

At some point doing less with free weights offsets whatever advantages free weights have in those areas where free weights have advantages. I don't know what that point is. Practical considerations of what motivates a specific individual to make any sort of decision associated with a positive health outcome are more important and useful in my opinion than this speculative masturbation about ill-defined theoretical optima.