I feel your message is the most important in this thread because it's the crux of the whole concern about privacy and the cloud.
Where technology has failed us most is in the utterly stagnant evolution and maturation of secure private networks. The following is a utopian notion, but had private networks seen as much R&D as the public clouds, they would be significantly less cumbersome than today's clunky VPNs. Imagine all of your devices collaborate directly with one another and with you on your own secure private network—no central cloud servers needed. Your personal assistant is software running on a computer you own rather than a third-party's centralized server.
I still feel this ideal will eventually be realized, but for the time being, no large technology company is willing to take the necessary risks to buck the trend of centralization.
The biggest fiction propped by up centralization and cloud proponents is that it would be impossible to provide the kind of utility seen in Cortana, Siri, Google Assistant, Alexa, et al without a big public cloud. A modern desktop computer has ample computational capability to convert voice to text, parse various phrases, manage a calendar, and look up restaurants on Yelp. Absolutely nothing the public clouds provide strikes me as something my own computer would struggle to do (to be clear, I would expect a local agent would be able to reach out to third-party sites such as Yelp or Amazon at your command in order to execute your desires, but they would do so directly, not via an intermediary).
A few years back, when Microsoft was at the beginning of its Nadella renaissance, I had hoped it would be the first technology titan to disintermediate the cloud and make approachable and easily-managed personal private networks a thing. Microsoft's legacy of focusing on desktop computers would have made it well-situated to reaffirm your home computer as an important fixture in your multi-device life. They could have co-opted Sun's old bad tagline: "Your network is your computer." But they elected to just follow the now-conventional public cloud model, reducing everyone's quite-powerful home computer to yet another terminal of centralized cloud services. Disappointing, but I think it is ultimately their loss. I suspect a lot of money is on the table for someone to realize a coherent easy-to-use multi-device private network model that respects consumer privacy by executing its principal computation within the network.