The trick will be to time your first camp well - wait for a good forecast and go for a one night trip.
Where are you planning to do your camping/walking, by the way?
I am planning on continuing the YWW with him. We did the first leg the other week, and I'm planning on doing the next couple of legs in Feb when he is off school. I'm starting to think it will be too cold then though, and I should leave the camping part til later. I've just watched Abbie Barnes doing the YWW on YouTube. She went in April and it was snowing in parts, so Feb could be freezing. The first part we did early January was a lovely day so I've forgotten how harsh it can be .
I am trying to get him involved, and as he enjoys a bit of cooking, let him do some on the trip (well away from the tent tho lol). Unsure of how else I can get him to feel more in charge and less of a kid though. Competing with the Xbox is difficult!