Well, since this thread is hopelessly off topic, I will chime in real fast. If the sole purpose of the league is to win at all costs (especially with large amounts of money on the line) then The Lung is completely right. You should wait as late as possible to hold your draft. However, if the purpose of your league is more aimed for a fun competition, then it should be held when all people will have the most fun. I personally enjoy having some earlier drafts in some of my leagues. Some auctions, some live, some slow, some late, some early, variety is the key for me to stay intrested. I hate having five drafts in August. For me it really kills the season. I get burnt out too early.
So there are legitimate arguments on both sides.