I've been reading his books "Teach your Own" and "Learning All the Time." The second book has lots of natural ways to work on reading, writing, math etc with one's children. The first is a bit more of a manifesto talking about the ways "school" hurts kids and how deschooling can help that. It's been updated a bit by Pat Farengo.
So many of the things he says make sense. His observations are acute and patient; his conclusions sometimes seem a bit naive and don't acknowledge enough the virtue of obedience. He seems to think that obedience and freedom are mutually exclusive; yet, I don't see him as actually believing that in practice. He says at one point that it's as false to believe that adults are big dysfunctional children as that children are little dysfunctional adults. I don't think he consciously thought in Rousseaun terms, but there were some reflexes in his thinking that seemed to limit the validity of his conclusions.
He seemed to unleash a torrent of "mindful" parenting -- parents who watched their kids, thought about what they saw, explored different options for learning. Sort of like Dylan and the Beatles unleashed a torrent of garage musicians. There seems to be a certain sort of person who makes other people feel they can do what he did. I think it was him who said that "leaders" don't look behind them to see who's following -- they just lead by doing. While there is a "charismatic" type of leader who saps their followers' freedom -- everyone tries to make themselves into copies of the charismatic leader. (I think there are different types of "followers" and some MAKE themselves into the second type, no matter who they are following -- think of Bob Dylan and his little hangers-on whom he tried to back off of-- but I do think he has a point about the two types of leaders).