Hi,
It sounds like your DS and polarbear's DS have some of the same issues as our DD (and also similar teacher issues). We are currently at a private school and the next level teachers haven't agreed yet to take her next year; we are trying to work it out. Previous teachers at that same school (and another Montessori school) were great; this year, not so much. I tend to ramble so will try to be concise. Here are a few things I wish I had understood before or done differently this year:
1) I wish we had *not* worked with the school psychologist for an evaluation (we thought this would help get DD in next year). Instead, from what I can tell, she based the evaluation entirely on questionnaires--mainly from DD's teachers who only mention positives on the way to complaining (at great length) about her behavior. Find a specialist in gifted/LD kids who can help.
2) (1) particularly because once you get an evaluation, schools in the know to which you apply in the future will ask you whether you have had one and please provide a copy. If you have a very unfavorable one, this puts your kid in a very bad position--private schools are likely to not want to deal with 'special accomodations,' in our experience. So then you are in a position of either wasting the application fee or lying.
3) We had the same kind of thing with DD's teachers this year--they suggested advanced math lessons from the school's own staff math resource person, but it didn't happen until four months later despite regular but pleasant queries on our part about when it might begin. I don't know what else we could have done except do it on our own--which we now are, with IMACS and EPGY. Very disappointing for a private Montessori school where one of the 'selling points' on the tour is that kids can work at their own pace and even go to the next level if that is appropriate. It did work with previous teachers, but not this year (okay, until Spring).
4) We're still working on how to address DD's dysgraphia. Voice recognition programs have not worked well for us; we are trying to encourage DD to keyboard but she has been slow to adopt. Actually her writing isn't so bad, just slow. Plus I have to sit with her anyway when she is doing word processing on a form because if her typing changes the formatting (i.e., in a Word document with previously inserted questions) she gets frustrated very quickly. But at least I can do that if necessary.
Best of luck; sorry you're having these problems.
Hugs!