So for payouts today, we're in the same spot as a couple days ago. Essentially I withdraw everything in Cryptsy (99btc at that time), and normally that would cover all of the payouts (we owe like 90 with the threshold). However, since the withdrawal took 5 hours, we now have 99btc in our local wallet, and owe 114 total. I've withdrawn the next set from Cryptsy just now. If it takes the normal amount of time (5-10 minutes), everyone will get paid at the same time. If it decides to take 5 hours (or anything more than the next 30 minutes), I'll send out a payment for whatever users we can, and the 2nd payout will come later tonight whenever the withdrawal goes through. I'll give you guys an update in 20-30 minutes one way or another 
its been said before, but why dont you just withdraw in more frequent, smaller amounts? if you're worried about large withdraws being the issue, this seems like an obvious solution.
Probably because most pool admins have a family and a real job. So this starts out as a side business. Which means they wish to spend a few hours
a day making everything work. But if they now have to spend 8+ hours a day babysitting a pool, paying colo costs, ddos costs, and etc.. and just now
making some ok money per day... they cannot exactly quit their day job or hire someone to assist them. The numbers do not work out yet especially since
it is a new pool. It is a catch22 for them.