Mooseman: I'm not so sure about trying to schedule around vacations. If they come up, they come up and we'll just have to wait it out. I think it'd be too hard trying to schedule bye weeks so far in advance. Besides, if games get played ahead, it wouldn't really make much of a difference, since anyone playing early would just get their games done faster and the vacations would still fall at the same times. So it's not like it would slow anything down.
Modus: Yeah, I agree that the 2 weeks might be cutting things short. That's why I'd like to try to match up people based on when they're online, to mitigate the effect of time zone shift as much as possible. Like I said, I think we'll have to play it out a bit and see how it goes at first.
I'm going to be keeping track of records and results in the first post of this thread. I like Modus' idea of pairings as they come up. I could create a schedule for the first week and subsequent games could start as soon as players are done. The downside of this is that a few players may get so far ahead that there's a long lag before the can play again. Also, you'd miss out on knowing your next opponent and looking forward to future games on the schedule. But things would certainly move along faster.