Pres, you need to get a copy of the rules and read through them carefully. Go to an AA CTO and harass them until they give them to you.
1. No, it doesn't start on your first segment. It starts on your first *international* segment. The RTW doesn't seem to treat US and Canada as different countries (much to many canuck's chagrin), so you might run into a situation where the clock starts ticking when you leave the US. Call the RTW desk and ask how this is treated.
2. Open jaws are permitted, and they count as one stopover. Realistically, this no longer matters, so yes, they are permitted.
3. You are limited in reservations by the amount of time ahead that the respective reservation system allows you to be booked. You can book a year ahead, but if a reservation system only allows 300 days, you can't reserve past 300 days. At that point, you have two options. First, do an open ticket and make reservations as you go. Something I don't suggest. I am finding that is causes a lot of problems, though my issues have nothing to do with an open ticket. What I am dealing with, though, is the same process and it is a real pain in the arse. The other option is to pick arbitrary dates, and change them as necessary. I did this on both this trip and on my last one, and it worked fine. You can't change routing easily, but you can change dates of an existing routing simply with a well placed phone call to *daytime* res or the RTW desk, or by stopping by a CTO.
4. You need to keep Asia, N/A, and Europe in one direction. East or west doesn't matter, as long as you are consistant. S/A, Africa, and Australia differ a little because they are north and south. Without going into a full explanation, get a copy of the rules. You will do yourself more good than you can imagine.