I volunteered at a microdairy for a while a few winters ago. Small herd, about thirty-odd + one bull, calves at foot for about a month, I think, then separated, some of the females kept to join the herd, males being sold off to a beef farm. The calves and mothers were still visibly (and audibly!) distressed by separation for a few days, then they appeared to get resigned to it. They got to stay out on pasture all year through careful management and rotation, though they might have preferred a barn when it got really wet. I don't know cows well enough to say for certain but they seemed content enough. Not without its problems as you note, esp with the larger scale stuff and the way cows have been bred into milk factories that can barely lift their udders off the ground, but then there's the farmer's reply that if nobody ate meat or dairy then the cows wouldn't exist in the first place. From a selfish point of view the milk, yoghurts & cheeses were delicious...
Haven't had the pleasure of meeting Fairlie or seeing him talk, though I did some scything with Gill one one occasion and she was very pleasant and outspoken without a filter, but in a nice way. Just found this vid of Fairlie debating Monbiot which I'll go and watch now: