We have been considering homeschooling but there are several problems. The main one is that he has always had difficulty with social skills and with some executive functioning skills and my hope has been that he could improve those at school. I know it's possible to do rich social activities as a homeschooler, but there are reasons that would be very difficult.
My experience is that for kids with lagging social skills, school does not help, and may make things worse. At our (former) school, there was relatively little time for socializing during the school day. And if your kid is perceived as different, he may be shunned on the schoolyard (ask me how I know!), and not invited to playdates for after-school socializing. So why bother trying to play with the other kids (and practice social skills) if they're just going to ignore you (at best). With this also comes the "there must be something wrong with me" thoughts, which don't help. (Of course, if your son already has a good group of friends, this may not apply.)
Plus, if there is a strong desire to be with other kids, there are other ways (Scouts, 4H, after school clubs, etc), in addition to getting together with other homeschoolers.
Me, I would homeschool. In fact, we did. DS is much happier, has more friends, and has more confidence in his abilities (academic and social). I would not say we have a heavy social calendar (there are a couple of days each week when we don't see other kids), but since the kids we do see actually like DS and DD, the interactions are more meaningful.
We pulled DS and DD out of school for academic reasons, not social ones. In fact, because of many of the same problems you stated (boredom, not willing to put in effort, feeling incompetent, all resulting in bad behavior). The improved social life is a happy fallout of homeschooling, and in some ways was a surprise.
