I've done two Iron Butts. A 24 hour/1000 mile on my TLR, and a 36 hour/1500 mile on my Hayabusa. Let's see. Where do I start.
1. Wear ear plugs. Thank me later.
I wear ear plugs pretty much every time I ride.
2. I think you'll find that any more than 2 people is 1 person too many on an Iron Butt style ride. Everyone has a different pace they are comfortable with, and everyone wants to stop at different times for fuel/food.
I think there will probably be 5-10 people on this trip. However, each person is going to get separate maps with the route on it and recommended stops. No designated lead or sweep riders. Everyone is going to go their own pace. If you get left behind, we'll either meet at a meal or at the mid point. Hopefully everyone will stay together though.
3. Don't lollygag too much. You'll have time to relax, but since this is your first, you'll be surprised how quickly it will pass by. If you can make it work, great.
This is probably my biggest concern. Spending too much time relaxing and then not getting in till 30 minutes late.
4. If you do want to certify it through the Iron Butt association, study carefully what they will require you to send in. It may not seem like much, but when you're on the road, it should be second nature. Take a little notepad to log your notes on, as well as enclosing them in a zip-lock bag to make sure it doesn't get wet. Take a pencil. Also, keep a separate zip-lock bag for all of your receipts. You will need those. Don't forget your start/end paperwork. If you stop for more than 15 minutes, you're supposed to record that. Documentation documentation documentation. I can't stress this enough.
We are going to certify it trough Iron Butt. Thanks for the tips on documenting everything.
5. Take bananas and sour patch kids candy with you. The bananas are good and healthy, the sour patch kids are good to chew on when it's 3am and you're pretty tired.
I think the plan is leave at midnight and ride through the day, in order to catch the Museum while its open. I'm sure I'll take some 5 hour energy and stuff like that in addition.
6. If you think it will start to rain, stop and get your rain gear before it does. PVC rain gear is 10 times harder to put on *after* it's started raining.
That is no joke. I've got some frogg toggs that are a pain in the ass when I'm already wet.
7. Don't overthink it too much and have fun!