With most of your points I would say - not skipping is not a neutral choice, it's easier to ignore potential consequences, but (for example) what if he achieves less because he switches off? What if he resents you not skipping him?
With #5 I totally relate. I am holding out hope to be able to send my HG DD to a private school by yr5. Right now I feel like she needs a second skip to be instruction at her level at our local public, but I am pretty certain she would not need that skip at the private school, so much so that if she does go private for 5th we may need to reverse a second skip... That's tricky. And it's absolutely not an option for us to just send her now.
