You'll probably start stimming during your period. I have started all mine on day 2 or 3. There is only a finite period of time to stimulate your ovaries before your body wants to ovulate everything out, so stimming starts pretty quickly after your period. For me, my period before a cycle is always pretty normal. It will likely be within whatever your normal level of fluctuation is for duration and flow. If it's very different and you're worried/curious just ask, the ladies at Genesis are really easy to talk to. (Hopefully you never need to find out because you conceive the first try , but it's the period after a cycle that can be a little crazy.)
For your planning nature, you'll have to do your best to last until day 1! Once you have that day pinned down Genesis will put dates into your chart so you'll have a good idea what the rest of your timeline will look like. People usually stim for 10-12 days then trigger. I stim for 15 or 16 days (I'm a slow grower) so don't be worried if it takes longer than the average 10-12 days. After your trigger it will be 36 hours until your retrieval. You'll get a feel for when you might trigger based on how fast your follicles are growing and Dr. K will talk you through that at each of your ultrasounds. They grow an average of 1-2mm per day (0.7mm per day for me!). Genesis will walk you through it, it will be easy!
My advice for working with Dr. K is to always ask for her opinion, good or bad. She always gave me all the information and then let me make the decisions, but sometimes I wish she'd have been a bit pushier with her opinion. I had one cycle that she thought we should cancel and thinking back on it she did say that a couple of times, but not strongly enough that I heard her through my emotions. So I pushed forward and lost everything that cycle. If I had listened to her from the beginning I could have cancelled that cycle and saved my money so I could do another cycle that may have had a better result. Again, she did recommend cancelling, but it's easy to get so wrapped up in the moment that you miss the message. So I asked her to bully me a bit more to make sure I heard what she was saying!