Re: Farewell, Cortana.
I'd politely disagree, that in the early days Cortana had been fairly solid functionally, and out of the "Virtual Assistants" she was the only one with a built up identity. The rub was that Apple, Google, and M$ all believed the lies or self delusion their engineering teams spun, that a fully synthetic ML model based the cloud would ever make it over the finish line.
Instead Bezos got Alexa running circles around everyone else because when the AI team couldn't deliver on their promises, he just spent the money to do it the hard way. Actual people, working their actual asses off to produce all the skills the other platforms lacked.
Now Alexa is essentially the only show in town, as Apple refuses to admit defeat publicly, but has backed off all but the simplest features of it's voice assistant. Siri isn't evolving, and isn't getting much branding love anymore. Google's approach fits nicely with dumping "free" almost but not quite good enough crap on the market so it can spy on you, and they think their personality free assistant is exactly that, good enough that they aren't trying to catch Bezos. The humiliation of their partnership with Nest didn't help.
Cortana could have succeeded in a bunch of different ways, but instead what could have been wins for M$ like the Skyrim voice port went to the competition because they were trying to make Cortana simultaneously cool and boring enough for suits. M$ could have inked deals to re-release the old Infocom catalog, or read storybooks, or a dozen other things to capitalize on the substantive personality and backstory they chose. Instead I think their management had a hard time envisioning anything other than a cellphone hands free assistant, and they killed off their phone division.