Good question. With the next pricing update scheduled to go live on Tuesday, October 10th, and all playoffs for Round 1 ending by October 14th (or 15th if we have any three-way ties for playoff spots), the 255M draft will be able to start shortly after. A four-person draft should take approximately a week, slightly more with the stadium round included, which puts us around Sunday, October 22nd.
I'd like to have all teams in by Sunday, November 26th (the end of Thanksgiving weekend in the States). Approximately 5 weeks from when the draft will end should be more than enough time. All owners should have three teams in at least two weeks before the final deadline, which is Sunday, November 12th.
I'll formalize this in a separate thread.