The only bits of interest/consideration:
I hate all the red tape we have today - most of what we do is common sense but we have to be careful.
How about drawing up some sort of Club/Rider/Parental Agreement.
Think of the various scenarios, as above, that you may come across whilst out on the club run and how you would handle them. Put it down on paper then get it signed by Club Secretary, Welfare Officer, Rider and Parent. - Just an idea.
What if he gets dropped and 1 rider drops back with him?
Try and have a named rider or couple of riders (someone who will look after the youngster)- not always possible as you don't know who will be on the club run.
What if he comes out with unsuitable clothing/equipment?
Advise him what he should wear, maybe have a chat with his parents and for the day see if you can loan him some.
What if he needs help?
Mechanical - help him to do it
A push up the hill - hold the seat post (not easy to do). Not the back of his saddle or pushing his back - unless you have his permission and, if possible a witness.
What if he needs a "comfort" stop?
If needs must, needs must. Find him a secluded spot and stand a short distance away with your back to him.
I know it's tricky but to fail to give him any help in any situation would mean you are failing the lad and failing to protect him.
---
I know exactly what you mean about over regulation stopping people getting involved in helping kids in cycling - and probably other sports.
I'm a Go-Ride and Track coach and have to face red-tape everytime i do the Go-Ride sessions. (How many of you wouldn't think for a second about raising a childs saddle - i won't even touch the bike without parental consent, just in case something goes wrong with the bike or the child has an accident after the alteration.) And believe me it has driven me and the kids involved scatty. The kids want to join a club but the local one isn't interested in having them, so they've asked me to set up a club for them. Back in the days when we were all younger that would have been easy but today it isn't. If you want to be a Go-Ride Club then you need to meet all the requirements and yes that is putting people off helping out. But in todays world it is needed.
If it wasn't for the red-tape then the kids would have had a club set up for them last year and we could have done the trips we wanted to do.
--
My wife is a leader for a Guide group and she's had to be CRB checked and needs to get permission slips for virtually everything, even going to the park across the road. She isn't allowed to take the girls in her car, and she can't take photo's without parental approval. It's all a bit different to how we operate in road cycling.
I remember one kid coming along on a club run a while ago, fit and keen but with clearly unfit father riding with him to keep an eye on him. We rode together most of the way, but then had a bit of a burn-up in the last few miles to the cafe. This was mainly inspired by the fact that this kid kept going to the front and riding really strongly, so we started 'racing' him. Of course, he had the time of his life and when we stopped he was talking about how cool it was. But unfortunately his dad (along with plenty of the other people in the group) had been dropped and fallen quite a way back. When he got in, he was clearly not impressed by the whole thing and we never saw the kid again. It was a real shame because the kid had clearly enjoyed the ride and the pretend racing, but you could understand that dad expected to be able to keep him in sight the whole time.
--
The rest of it's all "when I was lad..." stuff.