How will they learn self discipline?
So if these are part of unschooling how do they learn self-discipline, self-control and good life habits? Do you just use natural consequences for everything?
Talking to them about why we make the decisions we do (rather than why they should make the decision). Talking to them about how something make us feel. Letting them try things out. Helping them by making some things less odious. Making sure there are other options besides what they're choosing. Realizing that as competent as they may seem, that perhaps they really aren't as ready as we assume they are.
If certain practices are good, then do we need to train kids to do them or will they do them because they make sense? (Though not necessarily right away or on our time schedule!)
For instance, I've always brushed my teeth with my daughter. I remember brushing teeth as a child to be a long lonely tedious process so by doing it with her, I remove that one objection. Brushing teeth for her was also difficult because it wasn't automatic so she was conscious of doing it. By doing it together my daughter gets a social time which takes her mind off the tediousness of it. She's rarely chosen not to brush partly because she'd give up that social time. And skipping once or twice or even a whole week isn't going to give her cavities. It's habitually not brushing that will cause cavities. (But there's a genetic factor too.)
My dad just really has this thing about how school taught him discipline. He is a very disciplined guy.
If being made to do things until you can do them well makes people disciplined, then why isn't everyone disciplined?
Isn't it more likely, since only some people come out of school disciplined, that being a disciplined person is part of his personality? School didn't provide the opportunity to become disciplined. School provided the opportunity to do something that he got satisfaction out of: gaining new skills through hard work. That satisfaction didn't grow from nothing by being made to do something. The desire was already there. School just provided the opportunity to satisfy it. (Which wasn't the only source for that opportunity, of course.)
But what's the transition from me tending to his needs to him taking responsibility for himself?
If getting him to take responsibility for himself is your semi-conscious goal, then you're probably sending that message and he's going to feel pushed. Which will make him pull back if he's not ready to go. Make him feel like you'll be there forever and he'll feel secure pulling away when he's ready.