the grass is always greener on the other side

Before I pulled 9 yo out of school two years ago, I spent quite a bit of time agonizing over the decision: he was doing fine academically, OK socially, and he was not hating school. He was not loving it, and he did not have close friends who would sway him to stay, but I still had a hard time justifying WHY am I removing him from school. I finally took a deep breath, and just did it, hoping that this is for the best.

Now I am finding myself on the other side of the fence, agonizing whether he would be better off in school.

Reasons to send him:

• Schedule/structure: he likes to know what is going on, and how much time he is assigned per activity. I do not like it, and I keep getting distracted with other kids, so I am better off if our learning unfolds and takes as much time as necessary or available. Whenever I try to stick to a more structured day, I find myself in the role of a taskmaster, cajoling and yelling to move on to the next item on the agenda.
• Academics: while I have no doubt that he is learning a lot, and much more diversely than he would be learning in a classroom, I find myself thinking of projects that would be good to do with him, but I do not put enough time to implement them. He reads a lot of history, so a timeline would be so helpful. Why not write an essay about our family? Or make a presentation on chumash? All those would be so good, and so appropriate, but they would require a tremendous amount of effort and time from me, and I do not put it there. Why not? Because I have a crawling baby who is chewing on everything, and a 3 yo who keeps on wanting to be held, and 7 yo who needs one-on-one more than I can give. So 9 yo is left more to his own devices, and those tend to skew heavily towards reading and doing independent work.
• Social: in most environments, he ends up being the oldest of the group. That, combined with his natural desire to dominate, is not producing a pretty picture. He is not bullying, but he is forceful. Whenever he encounters older boys, he ends up in conflict. I almost wonder whether he would do better in a peer environment instead of having a group of followers.

Reasons not to send him:

• This morning, before breakfast was over, he wondered about the molecular weight of tomato sauce. Then he asked what would happen if we could tell what will happen in the future. Both of these led to the kinds of open discussions which I love having in my house. Most likely, he would not have time or opportunities to ask these sorts of questions in school.
• Academics: the coop that we are part of is offering classes which he would not have in school: architecture, history, war weapons. Online, I can pursue more programming classes. He spends time online researching things that are of interest to him. The field trips and opportunities for hands-on learning would be lost to long hours of sitting behind a desk. The independent and critical thinking skills would take a backseat to following the groupthink.
• Freedom: despite me wishing that he would use his time more constructively, he has more free time now than he would have in school. A friend recommended this article from the recent NYT which just underscores how little we value free time in our quest for busyness. It is hard to justify taking this away from him in return for a few good-looking worksheets and assurance that he is outputting something.
• Carpool/lunch/schedule: I hated having the whole day tied to the time I had to drop him off and pick him up. I hated packing lunch every day. I hated being on school calendar and trying to squeeze all family outings into Sundays. I did not like that he missed on all the day trips I did with the other two kids. If he goes back to school, there are bound to be hurt feelings about family experiences that he'll be missing.
• Tuition.
• Finally, since having one less kid at home would ease up my load, he would feel as a burden pushed out to make space and time for others. The potential for emotional resentment is great, especially when the feeling that he was the "easy one", so he got sacrificed for the more difficult siblings vying for paternal attention.

And yet, I wonder what to do. I am stretched too thin. Something needs to change. I do not like the general direction where my relationship with 9 yo is heading: squabbles, accusations and fights, suspicion, unhappiness. And then I know that I need to take a good look in the mirror at myself. This video just underscores that the traits that we do not like seeing in our children are the traits we possess ourselves.