I just did my first SS1k this weekend ( sat)
things I learned thus far ( still processing and recovering ( mentally, not physically)...
If your friend is hestitant about going, he is going to bail on the first gas stop.
Don't overspeed in VA, 15 over is reckless driving.
Even though it is going to be 90 in the day, it is still freaking cold at 4am.
Every little town on the map doesn't have a gas station.
Stop for gas in the big cities if below 1/2 tank, sometimes it can be scary coasting into to a gas station between big cities.
Go into the bathroom if you want to use Goldbond. People look at you weird shaking it down the back of your pants while putting gas in the bike.
People also look at the space range weird when he comes out of the bathroom with white powder all over his pants ( ie: be careful applying the gold bond)
Your GPS has no qualms sending you 5 miles down a dead end gravel road to find a restraunt that is on another road in the same city w/ the same name.
You can find a great views of the ocean at the end of gravel roads.
People living in beatup mobile homes at the end of gravel roads do not like you turning around in their driveways.
Put a new battery in the Autocom (or whatever audio device you have)
Make sure your Wicking biker Shorts are not short shorts. i didn't get monkey butt, but I got bad monkey leg. where my legs sit on the side of the saddle.
Sitting on the edge of the passenger seat, lets alot of wind blow on your bum and alleviates monkey butt/leg
You will run out of things to think of, then you will think of why you ran out of things to think of, then you will start thinking of things to think of that you never thought you would ever think of. At this time, buy new batteries for the autocom.
The day after your ride, you will be brain dead and dyslexic. Avoid talking to much, or you will say something stupid. ( My wife and I were drving to lunch, I saw a guy and his kids putting flashing on the roof of his house. I said " look honey, that man and his kids are working on the fence. Isn't that cool." I dind't realize I had said fence instead of roof untill she told me later. I did this all day, and everyone enjoyed it very much.
overall, enjoy the ride, pick a great 1/2 destination. I went to a marina and had fresh crab in VA. Got to see a classic/antique boat parade as well...