I can tell you, as a worked and experienced 1st AD, scheduling can be one of the hardest parts of preproduction. Depending on your budget, my typical method of developing a shedule starts first with locations and then I go to actors. The reason being, depending on whether your locations are public property or private business/residence, the Private sector will have a set schedule of events, openings, closings, and that kind of generic thing. I'm sorry that I can't really go into detail, just because it is so subjective depending on the script, director's needs, actor availabiltiy, location availability, equipment access, blah blah blah. It's for these reasons that film really is the most collaborative art form on the face of the planet. Anyway, back to the situation at hand. A few random tips I hope help:
1. GET AN EXPERIENCED 1ST AD!
2. Get ALL availability for talent and crew up front and quickly, a month in advance of shooting is preferable, but I've closed with as little as 12 hours before a shoot starts.
3. Figure out exactly what kind of shots you want (storyboarding AND shoot lists). Remember that a shot on sticks will take less time than a dolly move or Steadicam. For anything other than handheld or sticks, add an hour of time, thirty minutes if it's a rugged short film. Things always take about 1.5 times as long as a DP tells you it's going to.
4. Get ALL location info. Get permits (in writing, even if it's a friend. Ugly story about that kind of thing). Closings, openings, schedule of special events, staff on hand.
5. GET AN EXPERIENCED 1ST AD!
If you would like some forms that are commonly used for setting up shooting schedules, shoot me an email and I will send you some stuff from an old shoot of mine that you can take a look at.
Good luck. It's a daunting task, but somebody has to do it.
-T