The school where Obama's kids go in DC charges $29,000 for K. We just had this situation (cutoff 9/1, B-day 9/11) and kept our son in his preschool for a second year with the 4s-5s. He did much better behaviorally in his second year and was sort of a leader in the class, showing the new kids how things worked in the class. He started reading at 3.6 or so and was doing 100 piece puzzles at 3. he's not a 150, but very high in non-verbal. We didn't push for early entrance and DS6 is bored and complains that he doesn't learn anything. We didn't really know about the early entrance to 1st, which I think would have been the way to go. We are getting ready to push for a grade skip to second, but I think it will be harder than it would have been for early entrance to 1st. Since you mention dexterity issues, I think early entrance to 1st might be a better course. As for learning how to follow directions, etc. I would bet your preschool covers that. Hope this helps.