The other big question is how long do you wait? My son is starting K. He was not happy his last half of preK. He wasn't bonding w/ any of the kids, didn't like the toys. But how much of it will be adjustment to K? I can't get into the school to observe until November so that gives him 8-9weeks to adjust to the new environment and long day.
DS8, looking back, was depressed in K. I made him stick it out but it was hard and stressful for both of us. He still remembers it and talks about it. He commented that K ruined him just yesterday.
I usually fall into the trap of, conferences aren't' until nearly NOvember. By then, the holiday hoopla starts so things get a bit better. Then there is winter break. Things will pick up at school in January but then things get bad again by late Feb, early March. BUt then we limp along until Spring break. But by then the year is nearly over and I convince him to hang in a little while longer. Finally we got to the end of the year.
DS did reach a critical point where one morning he was blubbering and stomping his feet at the door as the bus is coming "I just can't take it anymore. I'm so tired of learning things I already know." He was just emotionally out of control. I kept him home that day. That is when the stomach aches started I think. My issue is not knowing what the real issue is. FOr him I think it's mostly personality. He's MG not HG+ like the kids here yet he seems to be acting so extreme. But he doesn't want to HS because he said he'd miss his school friends.