For me, part of the "wing-trying" comes out of my reminding myself that I'm raising future adults, not children. It becomes easier for me to do things in such a way to build resiliance when I keep in mind the main goal of raising our kids is to develop healthy, productive adults.
But then... I am not a pushover. I believe very strongly that if kids never hear a "no" that you enforce, then they never believe you mean it when you tell them that you love them either--you're just viewed as undependable. I firmly believe that if you say what you mean and mean what you say, kids respond with better behavior and stronger growth.
And...I am not and never have been a helicopter parent. I always half-joke that I practice "benign neglect" when it comes to parenting. I have always been the parent at the park who reads or talks to another parent rather than hovering where the kids are. I'm the mom who assumes that the kids are probably okay and not kidnapped by monsters even if they're out of my sight for a few minutes. My kids work out their own arguments at ages 3 and 6. (Does the 3yo sometimes get the raw end of the deal? Sure. But he also stands up for himself a lot more than many second kids I see. And the 6yo gives up a lot more than you'd think because he knows that things will be much worse if I have to intervene!)
I think giving kids opportunities to make mistakes has a lot more to do with the parents' state of mind than anything else, really. In fact, if you approach HSing with encouraging independence as one of your goals, it's quite easy to do. The kids have a lot fewer opportunities to follow the herd and a lot more chances to work independently in HS than in public school, IMHO.
Also, I find that being with my DS pretty nearly all day every day has really changed the nature of our relationship, not to mention his attitude. I've found that it's pretty easy to say "Go play!" when you're together so much. I feel much less need to micromanage his time than I used to, when we had all the pressure to get (dumb!) homework done before dinner, just at the time when he was at his most worn out and cranky. Now I let him decide when he wants to do things, and if they don't get done, there are natural consequences: no time to play, no TV time, etc. He definitely takes more responsibility for himself and his choices--and even for his education!--than he did before HSing!
With all that said, though, I think you do have to know yourself and your weaknesses to be effective at HSing. If you tend to hover, I think you're right that it could be hard to break yourself of the habit, regardless of how much time you spend together. And it can be very hard to be both mom and teacher. I've had to learn that it's necessary sometimes to stop teaching and just *be* together. I think it would be even harder for me to learn that balance if I tended to hover.
For whatever that's worth...
