I've posted before on this site about how I always felt like I knew my child very well. After homeschooling, I feel like I REALLY KNOW him. It's amazing how much I've learned, especially about his abilities, strengths, and weaknesses. We've only been homeschooling for a month, and while we're still learning as we go, I feel like ds and I are doing really well. He's learning so much, and like I said before, my sweet boy is back!
This is great and something that I look forward to. I can read DS better than anyone with regard to most things, and I used to see how much he was interested in learning, but I guess I haven't seen that in awhile (now that I'm really thinking about it). Truth be told, he's never really liked school, but I always just chalked it up to the normal 'I hate school, I'd rather play all day' stuff. I think as I'm reflecting on this, I'm realizing that there are signs we should have noticed, but we just didn't have any idea that it was that bad - by "that bad", I mean the lack of real challenge, that even his teachers may not have noticed because DS isn't/wasn't a squeaky wheel at school. I do know things about how he learns, but I just have a gut feeling that there's so much more to him that hasn't really been tapped into yet, and maybe that's what's causing me to feel like I don't know. Bleh, I feel like I'm rambling, LOL.
At the risk of sounding too idealistic, you do have access to someone who can tell you that kind of thing - your DS. It's his education, after all, and if you can get him to be a reflective learner that's an enormous gift in its own right. I suggest telling him you need him to observe his learning, starting with what he can observe retrospectively about what has helped him learn in the past. I expect he'll have trouble separating out what he enjoyed from what helped him learn (they do overlap, but are not the same thing) but maybe if you direct him to think about times he's started off thinking something would be boring or hard and in fact it's turned out interesting...?
Excellent idea, now just how to do it. I think that DS hasn't really liked school for so long that even he doesn't remember what it's like to enjoy it. Anything related to school is a big turn-off to him right now. I think that he feels that he spends all this time at school, and doing homework, and doing GT stuff, and doing extra required things at school that other kids and teachers think are fun, but he just doesn't. DH brought home a book for DS the other day (8000 Things to Know or something like that, DS has always enjoyed encyclopedia type books) and he was really excited. Over the next couple of days, all we heard were the various facts and things he'd learned while perusing the book. It wasn't required reading and I saw DS really excited about it - and learning!! As opposed to all the stuff he has to do in/with/for school.
We can't afford private school (a friend calls homeschooling "private school for poor people"!).
Too funny - DH made a very similar comment just the other day. We move around quite a bit and one of the main reasons we've been hesitant to do private school is because we're not sure we could always afford to keep him in wherever we may go. DH was in private school for a time and then went to public high school and he had such an awful transition experience, that he's adamant about not doing that to DS if we can help it.
It's not all roses, of course; unlike a lot of homeschoolers, I do in fact find the social aspect rather difficult, though it is gradually getting better (patience really is a virtue!); there are two homeschool groups in our community, one of which requires signing a lengthy statement of faith, which I cannot in good conscience sign, so that group of people is essentially lost to us. The other seemed at first to be entirely populated by radical unschoolers who wanted nothing to do with people who (gasp!) use any books; that set is certainly the largest and most vocal part of that group, but we are starting to find some other under-the-radar book-users, too, and finally feeling (in year four) as though we are acquiring a community.
This part of it makes me a little nervous. While I would most likely want to 'join' a group because I'd want DS to have some acquaintances/friends with a similar schooling experience, I'm the type that doesn't usually join groups. I like to make friends, meet people, and all that goes with it, but I'm also pretty content on my own too. I feel I'd have to find a pretty informal group if I were to go that route.
Oh, and opening up our yard to all kids has been a big help. We have THE yard for outdoor play!
LOL, I think I've got this covered. My house seems to be one where kids are allowed to come inside to play from time to time. DS was hosting off and on, in and out of the house, all day yesterday, as evidenced by my empty cupboards and full to capacity dishwasher last night.

Before "school" starts and at various points throughout the year, I always ask my son what he wants to learn about, and I tailor the year to those interests. It helps to keep him interested and invested in what we're doing. It also lets me make him responsible for his own education. It's not up to me to "entertain" him. That's something that really works well for us.
I hadn't really thought about approaching it this way, but it's a great idea.
Thank you so much to everyone. I really do appreciate all of the input and am taking it all in. I'm pretty sure I've broken some record for a marathon post and rambled on enough.
Thanks again!!