I must be one of those crazy dads

but my ive aquired 10" newtonian optics and on my trip up north to see the family my father my son and I will be making a truss dobsonian so we can fold it up and pack it in the car on our little trips out into the wilderness. It has the added bit that we have all made it together which makes it a very special and treasured instrument to which im lucky to be able to build.
As for your question the only thing that may become a bit tiresome will be that unless your boy is a giant then he is going to have to take steps out with him to get to a newt, possibly a refractor will be the easiest way to go as the eye piece will be at a more respectable height.
An easy Alt Az mount will be the best way to go about it do not get a GEM they are bloody hard to drive as they have few axis that they move on and if you don't get it roughy pointing in the right direction eg South Celestial Pole SCP it will be a nightmare to track objects.
so a little 80mm refractor on a ALT AZ mount will be the go, you can get them for well under 1000 dollars and in that make sure you get him the Almanack so he can see whats up every month with a few star charts, and possibly one of those little cards that has a twisting wheel inside that you can spin it around to the rough time and date and it shows you the stars that should be up. (ive forgotten its name). A little red head light torch so he can sort things out in the dark.
I always find making it special so a little box to all the goodies in makes the whole thing exciting because its "his" box for "his" astronomy equipment

matirialistic little buggers they are!
Brendan