Could this question be answered next Monday? I have to wait a week before I get all emotional, I guess.
Kiddo is going into kindergarten and has been very mercurial, to say the least. If I hadn't nannied with so many other families and already seen this, I'd figure it was behavioral instead of anxiety-driven. Yesterday, my husband and I high-fived each other for successfully getting through some potentially big and explosive transition moments with a lot of patience, smart thinking, and knowing what to say "yes" to. I know we've got a month or two more of transition bumps to get through.
This Thursday we do the testing, this Friday the teachers divvy up their classes. Next Monday, all the kinders go for half-day. Next Tuesday, it's the real deal.
My biggest apprehensions are that the testing teacher and his permanent teacher will be familiar with his vision issues and the short list of accommodations we are starting with, so that he doesn't start with teachers who are impatient with him. He has a diagnosis, so that helps, but it's hard to not be able to have an in-depth discussion beforehand. I also know that he's not likely to be the most challenging kid in the classroom, as he does have good self-regulation skills and knows how to be 'in school', so that in itself balances things out a bit for me.
My other concern is that he gets some opportunities to make new friends. We believed in sending him to the neighborhood school so that he could have friends in the neighborhood, but can you imagine? We have five kids on our block and he's the *only one* going to the neighborhood school (which is very well-esteemed.) The rest of the kids are in Japanese magnet programs, environmental school or homeschooled! Just looking for a new good buddy for him!
Okay, I wrote quite a bit more than I thought I would! Guess you know it's on my mind!
ETA: in answer to one of your specific questions, I think your expectation of getting homework started is a good one. I did this with the kids as a nanny; I used to make an afternoon snack (or have Tea Time, which some kids loved) and after eating, we'd settle down to work for a while. At this age, the babysitter should be able to help with the homework, no problem. Just make sure to A. make it ROUTINE and B. offer the snack first. And maybe the rule of no media/games etc. until both kids are done with their homework. If no homework, they could do some sort of other quiet thing...Homework/study/quiet play time.