The Gramercy Tavern beetle story makes me wonder about this. If you provided unified customer experience in some contexts it's cool. In others, it's creepy. Even if the actual act hasn't changed.
Self mockery, I guess. If you're a fancy restaurant, it implies that you are high end but not arrogant enough to ignore your own mistakes. So, it conveys the message that you are always willing the best for your customers.
It comes down to whether the experience is desired or not.
When multiple people recognize and respond to you, it is a sign of fame and respect. People generally like to be well-known and respected, so this coordination is appreciated.
When a machine recognizes and responds to you, it is often not a sign of respect but a sign of exploitation. I think it's kinda useful when I see relevant ads on a website based on my recent browsing. But I might feel differently if I spent 8 hours a day driving wherever a computer told me to go or cooking whatever a computer told me to cook.
I wonder what separates the two.