My suggestion is that if the school wants to provide him a Chromebook, let them. If your DS has a different type of machine, running different software, then he'd have to use methods completely different from those of the rest of the class in order to accomplish the same things. That's fine if you're a computer-savvy adult, with access to documentation and other support resources. It's less fine when you're 8, and the only adult in the room is learning the technology along with you.
Now, if we're talking about giving him a second machine for strictly home use, that's a different conversation.
