You sound like you are doing a lot to make your child responsible, that it really great. In response to your second statement, you reported you don't have a lot of time for fun or transition, but this may be what he needs, even more that the sleep. Kids, especially sensitive ones, need time to transition, need QUALITY time with parents and sibs. Most folks do have a busy schedule these days, but, (i don't know what your finacial situation is) you may need to consider what is more realistic, more money or increasing your childs life. This is not to sound judgmental, many parents would frown at such a statement, but it is often a reality that many people are willing to address as part of a solution
I know that is not the full solution, not at all, but think about increased time you can give the kids to transition from one chaotic event to another. In all reality, also, take the complitments from the professionals, because they mean it.