Soulfly, you are most welcome, matey.
Look, I don't want to try and teach my grandmother to suck eggs but you may want to consider, instead of handing the business over to your family lock, stock and barrel, bring a select few in earlier as management partners (<50%), teach them the ropes, slowly take more of a back seat yourself but still watching closely from the sidelines until you can trust them completely, at which point you hand over decision making to one individual. That way you know the business is in safe hands and you still have a controlling influence with an open door back in if the flying doesn't live up to your expectations.
You will have doubts along the way - I have yet to meet anyone who at some time doesn't start to question their decisions, especially when training aircraft go tech, people start shouting at them, the ATPL exams seem like an unclimbable mountain, you start realising how much it is costing, I could go on and on...............I felt this way flying back home from a recent aerobatics course, alone in the 172, tired after a long day's strenuous flying, done enough X-Country flying that it is quite routine and to be honest I was bored and I started thinking whether I really wanted to do this any more but it passed over.......but if it does get to the point where you really want no more then you've still got your business.
What I'm trying to say is that you may wish to keep a finger in each pie until you know exactly where you're going.
Onwards and upwards.