@Mark, what books are you reading? Are you following a training plan? That would be the easiest way to answer a lot of your questions. I follow Fink's Be Iron Fit plans (but with longer cycles than recommended) in his book, but I wouldn't advise you download it on Kindle. It's a reference book, so best in real book format.
One thing I find useful is doing my research well in advance. I read every page of the IM website several times, and printed off the pages and Q&As. Your success on the day will depend a lot of how you've trained, but also on your logistical preparation for the day. Usually the websites are very good with maps and lengthy instructions about how things work. There are lots of websites in nutrition and hydration for IM too so you can experiment with different food and drink in training.
I had two bottles in the cages along the down tubes and then an aero bottle stuck in between my clip on bars. The aero bottle was great, especially in the heat of the Outlaw, because the straw was always an inch from my mouth so I definitely drank more than if I used the cages alone. As Seren said there are loads of feed stations, and I would grab a bottle and top up my aerobottle while rolling.