Michaela - Is option #3 that you continue as you are and teach him to communicate his needs more and more clearly, concisely and succinctly to increase the chance of being listened to AND work on "adults don't always have time to listen carefully to every child in the group"... He's likely to get better at both things before school yes?

My 2.5yr old is exceptionally clear about communicating most things but certain situations she clearly just doesn't have either the cognitive or possibly language skills yet. It is almost always when I am asking her a question and she cannot answer. This morning:

Me: "Can you tell me WHY don't you want to go into the ballet class?"
DD: "I don't want to go in"

repeat ad infinitum. Should I put reasons into her mouth ("Is the music too loud?")? Should I give up? Mostly I give up. OR:

Me: "Would you like option A or option B?"
DD: "Yes"
Me: "Option A or option B?"
DD: "Yes"

We don't have these communication fails often but when we do the timing is always horrid... But I know it will pass and she's so far proving to be very likely to be listened to by other adults because she does communicate exactly what she wants or needs with perfect clarity and simplicity. She's ahead of where her sisters were in communicating with random adults, but all of them were pretty decent at being understood and listened to by 4.

It is prehaps naive of me but I think that this may not be as bad as you think it will be by Kindegarten. I think you can really make amazing progress both his ability to politely, clearly and concisely convey what he wants/needs AND on his ability to cope with not being heard at times.