I was travelling to the US a few times during previous administration and each time somebody from the team was taken into little dark room for questioning, I was not travelling to the US much before so I was of opinion the way how US border treats travellers was weird to say the least, at least compared to other countries I was travelling to. Sometimes it was worse depending on particular border agent. Interestingly I travelled recently during new administration and did not notice much of a change.
We were travelling for business from EU. My feeling was that those of us who were travelling most frequently were pulled, but apart from slight inconvenience it ended OK. We started placing bets who will it be this time :) I always had paperwork ready, letter from business I was visiting, hotel booking, phone number to business rep who would confirm my credentials, but I was never asked to produce them. Though, I don't know about travelling with family, I am not much of a touristy guy..
My own brother had a Canadian border agent screaming and shouting at him when he went on a business trip to Canada from the US. Screaming at him about why couldn't a Canadian do his job instead of having to fly in an American.
Canada is no better, if anything they're worse in this regard.
One anecdote doesn't support that conclusion. Talk to anyone who travelled to Canada and the U.S. frequently, about how the two compare. I used to work in academia, and know many people who travelled to both places every year for the past 20. Of course there are exceptions on both sides, but the default is overwhelmingly: Canadian border is friendly and welcoming, U.S. border is hostile and depressing.
