Thank you Allen, Julian and Ken.
Allen - Thank you for the warm welcome and great to hear your opinion re the Skywatcher dob!
You make it sound quite simple, although I am worried about the conflicting information re: ease of use/maintenance. I presume this is the sort of thing that becoming an ASV member would help with though - teaching him how to care for it? I will go and check out that Stellarium program - thanks!
Julian - yes, he would definitely enjoy planning and writing lists to tick off and note down his observations. He has an iPad mini that we can download some apps onto so I will have a look at SkySafari as you and Glen suggested, especially if they are likely to have lists compiled already as that would be helpful for the both of us.
Ken - thankfully my son is quite mature for his years and likes to follow things to the letter as far as instructions and things go, so I am sure that whatever piece of equipment we choose he will be respectful and not play around with it and will likely tell ME when I'm doing something wrong!
Given his nature, do you still feel that a dob would be impractical? I will go and google the ED80 now and check it out, and thank you for your advice re eyepieces