Hmm, it looks like you have a lot of difficult issues with your DS. I can't really speak to most of them but did want to chime in on the MAP issue. First, it is definitely not a hill to die on - save your ammunition on weightier issues. Second, at least for my kids and some of their friends, there were huge differences between math scores in the 250's vs. 260's vs. 270's vs. 280's vs. 290's vs. 300+. My mathy DS was able to score in the 260's with only elementary math but went up incrementally each year with the addition of Pre-Algebra (4th), Algebra 1 (5th), Geometry (6th), Algebra 2 (7th), and Pre-calculus (8th) in subsequent years. He needed Algebra 2 to break into the 300's. DD, who was not individually accelerated so did not take Pre-Algebra until 6th grade, demonstrated the same pattern although she was almost ten points lower with the same math school exposure. It is true that the 2-5 test may not be as accurate at the tail end due to fewer questions at the requisite level, but I know of students who score in the 290's and even 300. DS did not move into the 6+ test until he finished Algebra 1.
Another thought I had was that perhaps encourage your DS to complete the MAP tests, especially the math sections, within the standard time. While it is supposed to be untimed, our schools did not budget more than an hour and a half or so for each section. Almost all the kids finished within an hour or so. DS tended to finish within half an hour. DD used to dawdle and needed to go beyond an hour but that meant returning to the test a second day. She claimed that she needed the extra time to score her highest because apparently if you take enough time you can eliminate most incorrect answers and get points on some topics you haven't covered. I told her that wasn't the point of the test and that she needed to complete it within the first hour (class) for a more useful gauge of her actual achievement. She complied and while her scores may have been slightly lower, she was happier not to have the stress of testing into a second day ( missing classes and fun stuff).
