> I see a lot of people celebrating Windows 95 as a high point, and it isn't really a surprise - that was one of the last times that Windows had to genuinely attempt to compete economically for their OS share.

That might also have been around the last time when people expected to pay for a new operating system. The other thing Apple has done is to lower the cost of OS upgrades to the point where selling the OS itself has become economically difficult. Apple simply offsets that with insane margins on the hardware, MS doesn't have that option.