Thanks DeeDee. DS will be attending group therapy sessions with a handful of other kids his age starting next month, so I am hoping that will really help. We'll keep working on it together at home, and I'll make sure his regular counselor knows we are working on it, I'm sure he can help some as well.
My thought for the iPad app thing was that he tends to want to withdraw for a bit when he gets home from school (probably just a bit overwhelmed from the day) and instead of him just reading or playing minecraft, I could have him play a game that's meant to help his social skills.