You should wear your chaps from the get go. When you are in the wind all day, they are not noticeable. Eat light. But eat. A small bag of almonds and a small bottle of gatorade are perhaps the best purchases at refueling stops. Lot's of energy and no heavy weight in your belly to make you sleepy. Get plenty of sleep before you start. Carry energy bars and water with you. Those too are light but extremely nutritious. Carry a pair of long johns. When the sun goes down you can change into those. A heavier set of gloves will make you happy when the sun goes down. Might think about an mp3 player. Helps with the fatigue after four or five fuel stops. As far as your rear end goes, either you buttocks can take it or it can't. You will find out which category yours fits into. Use the rear pegs sets. Nice lay down position. Yup, you will be all over your motorsickle. When you have a hard time concentrating, it is important to pull over and collect yourself. A five minutes respite will help vastly. Another tip is to eat at wendy's. No not one of those numbered menu selections: A hot cup of java and a hot cup of chili. Works wonders for the core body temperature.
Regarding the chaps, wear em for those instances of light rain and asphalt protection. They will keep your legs dry. Also, a non perforated jacket that will repel water just long enough to ride through a light rain. Saves loads of time and once again, while at speed, they are not burdensome.