I'm not sure what internal incentives in the company lead to such terrible naming practices.
Same with .net — Framework (up to 4.8 I think) is Windows, newer stuff (Core) is cross-platform. So this Framework release from Wine is for stuff that ties heavily into Windows, which is why Microsoft gave it to them in the first place.
PowerShell is more than just "similar" to Windows PowerShell; it's a slightly-backwards-incompatible new version with cross-platform support. With cross-platform support, the old name didn't make sense any more; and presenting it as a "new" product solved the issue of people complaining when they upgraded and things broke. (Same thing they did with .NET.) I don't know what else they could have done here.
"Copilot" is Microsoft's name for their LLM functionality across all their products. Question in, slop out. That's entirely consistent. I'm not sure what difference you're even seeing between "Copilot" (which Copilot?) and "Github Copilot".
Azure DevOps was them renaming an existing product to coopt a better-known brand name. Same with Visual Studio for Mac. (Visual Studio Code and Azure Data Studio were similar - although those weren't renames but rather a new product trying to steal mindshare.) This is the only category I'd really call "terrible".
I suspect overthinking is the root cause.
Microsoft is no stranger to what's very transparently a bastardized form of nominative determinism, meant to sabotage the playing field by confusing generic and branded nomenclature. It's the opposite process to genericizing a trademark: you take as many random words as you can get away with, and turn them into brand names while nobody is looking. And then... you are suddenly everywhere they look.
So, a clear totalizing influence; its purpose: to tombstone a consumer product into the early termination of any attempt at independent thought - until thinking remains purely the domain of machines (that everyone is forced to trust) and illiterates (that nobody believes). Never succeeds for reason of some natural law or other, but it's a pain in the ass, a.k.a. a great motivator of economic growth, especially in epochs where imagination is frowned upon, like our present one.
https://en.wikipedia.org/wiki/Generic_trademark
Far from limited to Microsoft, either. Though theirs are particularly crude - someone else mentioned COM and .NET. Well, why would you even name a proprietary runtime platform something as plainly idiotic as "dot net" - except to mount an attack against the networked commons? Take "Windows", for fuck's sake - at least they didn't name a statistics package that. What about "Meta", and their "Messenger" - remember when all chat apps were called messengers? Privatize the entire "Alphabet" - then nationalize it, then repeat a buncha times!
https://en.wikipedia.org/wiki/Trademark_distinctiveness
These kinds of organized attacks against language are nothing new. They just take a lot of entrenched mindshare to pull off in the first place, so are usually the domain of actors of nation-state and transnational caliber. One of their side effects is that people become technically unable (not just unwilling) to learn from immediate history: while the spectrum of observable reality remains covered by a network of interlocking notions, the boundaries between notions shift. So, the most important nuances become impracticable to translate between those established mental models that precede the attack, and any newly elucidated ones. So a lot of wheels end up having to be reinvented. Sometimes entire bicycles. Like I say, great driver of economic growth - just like many other more obviously horrible things.