I wonder what type of preschool it is that your son goes to. Both of my kids went to/still goes to play-based daycare centers (not Montessori), and it is good experience for both. These centers don't have much structured play, they do circle time, sure, but that doesn't take much time. The rest of the time is divided into outdoors, puzzle time, reading time, role-play time, etc., during these activities kids can choose whatever they want to do under the general theme. The teachers simply guide the kids in whatever activities that the kids choose, and they watch the kids, figure out what they might need and provide them with it. At puzzle time, for example, a kid can be doing a four-piece puzzle while another busy with a 100-piece puzzle. At reading time, some listen to a teacher reading to them; others read to the teacher. At math time, some might do simple counting games, one or two might be doing division games. I remember once I was really impressed by a few kids who were looking at a world map together trying to locate the places that they (or their parents) had been to. I really liked this arrangement because the open-ended activities give everyone something that's appropriate to their levels. For a while my son (the year before he entered K) was really into World War II and the teachers let him bring his favorite WWII books to the daycare, read with him, copied pictures of tanks and airplanes for other kids who got interested in the books. And I remember my son once built a huge "river system" in the yard over several days and all the other kids were sailing their boats in it. And once the teachers told me that they bought a bunch of new math toys which were more advanced than what they had, because my son would be ready for those very soon. I'm not sure what my point really is. I guess it's that non-Montessori schools can work out well, too. You need to find out how much flexibility they have, and how willing the teachers are to let the kids take the initiative.

Anyway, my kids have had/is having a great time at daycare. So when DS entered the public school system, imagine our shock!

Well, without knowing your situation I might have just written something totally irrelevant. But here it is anyway.