Jay's experience is never in question. The boat, properly maintained is not in question for this
passage. There is no question about the abilities of a 16 y/o and a 32 years experienced sailor and as Jay points out - you gotta go sometime.
What is in question, and the only question, is contingency time and contingency
money. The farther you get from home the harder it is to maintain a schedule and if you have to fix something, it gets complicated.
Jay is taking wise counsel that
bermuda and back in 3 weeks leaves almost no contingency time. I would never in a second hesitate taking my son (10) on a two week sailing trip. That is value for moeny beyond words.
Head out Jay, go as far as you can in 8 days and then
head back. You've got 5 days slack in there.