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Notes -
Some of the problems are downstream of hardware vendors. Boot from sleep and charge problems are well-documented for how hard-to-reproduce they get, but also probably specific to firmware sleep mode support on various hardware being dumb as a sack of hammers. While it'd be nice for Microsoft to enforce various OEM requirements more stringently (or even to take a harsh hand in enforcing BIOS behaviors other than the stupid TPM clusterfuck), I think at least part of this trades off against the increasing variety of capabilities and options that motherboard manufacturers have been able to give out, and while some of that latitude has given us Asus, I'd still take that over Apple charging an arm, leg, and a first-born child for a soldered-on NVME module.
((And knowing MS, we'd probably lose Framework and keep Asus as the new standard.))
But there is a general trend toward worse user interface, in places that are software-specific. In addition to the problems you've already mentioned, Windows Start Search uses the web before local files or even applications, settings menus repeatedly disappear or get moved for little cause, and a variety of first-party apps range from bad to hilariously error-prone.
The standard argument is that Microsoft is no longer selling products, but advertisements, and these decisions either reflect those pressures (adding more interstitial buttons to charge a setting provides more marketable data, somehow), or are downstream of the old pressures no longer existing (Microsoft no longer cares if you prefer an old UI, cause they're not selling to you).
These are probably part of it, but the same issues have shown up in other companies as well, including many who either don't have the same pressures or who have always been in the ad business. I think the structures of managing programmers itself has gone tango uniform, especially in FAANG environments, such that building a slick new view has become far more important to careers than any underlying functionality, either intentionally or as a side effect of increased review of code that could invoke regression testing. There's some fair arguments in favor of this behavior over the old one to some degree -- the Windows Format Disk dialog, rather famously, was the result of putting code over UI, with corresponding Fun edge cases -- but the pendulum has definitely swung too far one direction.
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