Yes, I agree that it's not the optimal outcome. (I should have not used "win-win" and instead used "win-win for some consumers.") I was trying to emphasize the individual consumer only having to pay what they were willing to pay- not making a judgement call on what is optimal.

Furthermore, The scenario you highlight is price discrimination to the first degree, where the monopolist captures all the "surplus." Economists generally claim this outcome to be "unrealistic" but it helps us understand the more traditional outcome: https://courses.byui.edu/econ_150/econ_150_old_site/images/8...

As you can see, there is still consumer surplus from a monopoly price discriminating, but at the cost of a deadweight loss.