The Olympics will provide a significant boost in the all-time worth of some players (Will Luongo back another Olympic gold and put doubt to rest? Will Weber again be the tourney best dman? Will Datsyuk be MVP? etcetera). So, a mid-January start will get us to the middle rounds by the end of February, where many of the contemporary midcareer stars are drafted, making for a dynamic discussion of the Olympics and the draft side by side.
Ideally, the all-time draft should start
as early in January as possible, to be finished by the end of April rather than the end of May once again. Perhaps 2014 will be like 2011 was and we get an ATD, MLD, AAA, Double-A and Single-A Draft in again, another 2000-pick year!
Establish a hard and fast deadline to join (e.g., December 31st or January 10th and simply not have the clock start until like the 15th to accommodate any late holidayers).
The sooner a start date is set, the sooner a deadline to join can be set, the sooner active recruitment can be done.
The only disadvantage of having sign-ups begin in December is that Christmas is a hectic season for many, though it doesn't take long to reply to a PM and post "Hey, I'll be drafting a team in January" and recruitment could begin before the holidays and stretch right through to the new year. Of course, if that is done, there might end up being 40 teams!
Perhaps get a poll going with "beginning of January, middle of January or late January" options.