Apologies for my delayed response - crazy week!
Blake went along to the Junior ASV meeting on Friday and the poor thing really struggled. After 3 attempts at going inside, hyperventilating and retreating back to the car twice, he finally made it in to listen for a little while. The next day he said that he really enjoyed it and wants to go again but I think it might take him a little while to find his feet in this social setting. He was determined to give it a go though so I'm pretty proud of him!
Julian - yes, that was a very open ended question wasn't it?

I should have said 'essential' gear that he would need but by the looks of that app, I think he will have a blast like you said with just that and a new scope. Good idea re: a book - I will try to get my hands on one as he has a birthday coming up next week. As for Astrophotography - B was pretty impressed with the pics that some of the kids at the meeting had taken, so I do think he would enjoy the basic side of that too. We have an old dSLR and P&S that he could use - I will suss out the requirements for that down the track once he has found his feet.
Thanks for the eyepiece suggestions Brent and for sharing the specs of those scopes of yours. Off to research those! Cheers