I'm coming back to this post because DS' feelings about school haven't changed.

Deciding to sit in and watch him go through his day, I went to his school and observed for two entire days. I took notes hoping to see a pattern emerge that would give us a hint as to the problem. Nothing has surfaced. My and my husband's opinion about the teacher haven't changed; we think she's doing well. The work seems appropriate for him, and the environment is also satisfactory. The kids are all well-behaved and no bullying is going on that I could detect.

The one thing I did notice during my time there is he seems to be somewhat isolating himself on the playground. He doesn't seem inclined to automatically play what everyone else wants to. Instead, he is okay with going off and doing his own thing. If some other child joins him, he's happy to have them, but otherwise doesn't appear to make much effort to invite interaction. I was dismayed to see him acting like this and asked the teacher if he does it all the time. She said his best friend was out sick and that may account for it. I think DS is a more one-on-one type of kid if that makes sense. He's not a sporty type and most other boys and some girls are, so perhaps that is also playing into his choice of activity during recesses.
Ironically, recess is his favorite part of the day outside of math.

DS recently said to me, "No one is helping me with not liking school." I think he's feeling unheard because we've been unable to make things different. Nothing has changed at school or home since I first posted, btw.

Thinking we needed to bring this up to the teacher in more depth, my husband spoke with her about this again last night after PTC and she seemed concerned. Her prior reaction was one of surprise, but no conversation was really able to happen at that time since it was during school. In the course of conversation, she offered to try to tease out of DS what is bothering him. I hope she can. My husband and I are stuck on what to do.

Meanwhile, I've purchased a journal for him in the hope he will sort out exactly what is bothering him through the comfort of writing down his feelings and thoughts. Other than that, I'm out of ideas.