LOL, Hotmail checked every single box for what NOT to do with an email service. I still have my hotmail account. I still get spam on it. Hotmail's spam filter was basically a placebo. It was even worse than Yahoo, and Yahoo was pretty bad. I will never ever trust Microsoft again for webmail after my Hotmail experience. It was a huge waste of my time.
Most people do not want a digital assistant to be their best friend...they just want it to work. Cortanna and Siri's "personality" is exactly what I would use as an example of a gimmick feature.
Microsoft already tried this crap with that stupid paperclip avatar in Office...which everyone grew to despise so much it became a cliche of itself. When I say everyone hated it I really mean everyone. I have never come across a single person who thought it was cute and added to the user experience. Mostly people were trying to find ways to turn it off.
Which is exactly how search should be. It's a tool. It does not need fluff or gimmicks.
LOL, I have seen tons of examples like this:
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I tried this again, just now, on Bing. I got the same result. Everyone I know hates Bing too. Not as much as the paper clip avatar, but close.