Since you've asked twice, though I don't see the relevance; No, I don't have kids, however, I grew up on the water, been sailing/boating since I was one or two. So I'm pretty sure I'd raise kids exactly like me. I've been taking trips to Catalina Since I was about 12 with another good friend the same age, by ourselves. No Adult. So, yes, I think I'd allow my children to do the same.
I think I'd trust someone who said they were racing dinghy's much more than someone who claims to have raced on their friends 40' Catalina BTW.
I hope he gets through it ok and he probably will. Hopefully he posts some pictures so we can enjoy his adventure. I wish him well.
Sounds good, lets leave it at that.