I generally like the Warren Buffett approach.
Buffett Family Values: How To Raise Well-Grounded Heirs - Forbes
Handing out cash to friends and family who never learned how to manage it doesn't accomplish much IMO (Paris Hilton?). Putting family members in a position to leverage philanthropy seems to have much deeper and longer lasting results. My family does this now on a much smaller scale offering annual college scholarship awards to students chosen by their music directors. This can be done for as little as $10k and positively affects the lives of students who have never been recognized for their achievements.