I tried to get my DD into the MOntessori and was told the waitlist was a year and a half long. This was years ago, but I am told the situation is still the same. There are very limited spots available for their free preschool program (see below) that all get filled by kids who were already there.
If this is how you feel going in, how will you feel after four months, with six more to go? Steiner's ideas on child development are pretty rigid. I presume that many or most of the people who commit to working at a Waldorf school have faith in the philosophy. Where does his prospective teacher fit in there? How will s/he react to your son and treat him? Is there a risk that he'll spend the year among people who think he's damaged because he can read and do math?
The school and those who go there are actually a fairly big part of my life already. I do think it's all kinda nuts, but I also don't attach ALL that much importance to the philosophy if it works for my kid in practice. It will bother me, but if he does well with it, I can deal. However, I am sensitive to people acting like my kids are weird or "off" in some way. Ask me how I know.
So yeah. In thinking about it, that's a major concern. But I do know the director and find her quite lovely. She is great with kids and seems to enjoy my children.
I am pretty good at biting my tongue and am actually very crunchy in many ways. We would fit in fine if we could just nt roll our eyes at certain moments.
Last question: why is preschool so important? It's not like he's going to get any academic enrichment. So that leaves playing, which he could do at day care. My kids went to a family day care place and still go back because they love it so much (my youngest is 7). It had structure like a preschool.
He is at a small family daycare now. We love it, but he is really outgrowing it. In my state free, universal preschool is offered in the 4 to 5 year, but almost never at in-home places. This means that if we want to take advantage of the free schooling and if we want him with age peers, we need to go to a larger center or preschool of some kind. If I thought the place where he was would continue to work, I'd keep him there in a heartbeat, but she doesn't really even take kids that old.
I don't care about academics in preschool at all and would rather avoid them. I want him in care so he can play with other kids, get practice in doing school, and enjoy the kind of fun and creative art/play projects I don't really do much of it at home.
FWIW, his current daycare provider is familiar with the Waldorf and recommends against it for him--she says he would be bored.