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.
I think it has a lot more to do with nostalgia goggles. Windows 95 still had a lot of the same cruft on install. It really wanted you to sign up for an MSN dial-up account to use the bundled IE to browse MSN.com as your home page "of choice". Another bundled app suggested a subscription service to get and send Faxes.
(Windows was always like this. It seems far more "extreme" now, but the roots are deep and old. A lot of regular Windows users don't even notice what Windows 11 is doing because the frog has been boiling in that pot for so long.)
Don't forget was Windows 95 that became the anti-trust scandal because a lot of people felt at the time that Microsoft didn't have to genuinely attempt to compete economically for their OS.
(Same as it ever was.)
My point was that in contrast to today, where consumers have windows, and pro users are turning to non-windows alternatives, in the late 90s Microsoft themselves provided the pro user alternative.
Perhaps Microsoft intend LTSC to be that pro alternative, but as you say, thats not available to everyone.
There's genuinely no economic incentive for them not to sell their own OS down the river at this point.
Mac has established itself as a only-on-mac-hardware market, which rules it out as an option for the majority of corporate and educational settings, and while I wish the year-of-the-linux-desktop was actually coming, most coorporations just aren't set up to / don't understand how to manage OSs without the fallback of a company guaranteeing support.
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.