As far as AI work, I personally really appreciate their emphasis on privacy, and that kind of work seems like it would be a lot harder (or nearly impossible) if they were collaborating with another company. I'd rather have a subpar experience and my privacy than a great experience and my data being sold, mined, subpoenaed, or otherwise being made accessible to systems/organizations that I'm not aware of and don't consent to.
As far as the iPad Pro, I don't own one but when I replace my aging iPad I plan on getting a Pro with the pencil and keyboard because 1) these are features I wanted and I don't mind if someone else implemented them first and 2) all the reviews I've seen about them say they nailed it with their own implementation. I don't think they could've done that in collaboration with MS.
If they don't somehow learn to do it, they will be eaten by Google and Facebook; the money is not in the hardware anymore. A decade from now, it certainly won't be.