I did the ride 15 years ago. If you can find a group - or organize a group - to do the ride with you'll have a better time. Check with your local bike shops and see what they have to say. (I did a quick web search and there are quite a few gay cycling clubs around - so you should be able to join up with one to do the ride.)
If you go with a club, this may not be necessary - but... I'd also recommend that you pay close attention to when the route is announced so you can call and get hotel rooms in as many of the overnight towns as possible. The tent camping in fields and parking lots wore me out more than the cycling.
Oh god, DON'T do RAGBRAI. My parents live in Iowa and the weather that week is horrible! It's hot, humid and nasty with bugs. and you are in the boonies across the entire state - there's not any break from this weeklong nightmare.
I did RAGBRAI two years ago and had a blast. If you can ride with a friend or a group, it's better, I think. I rode solo but met lots of interesting people along the way, but it would have been nice to share my tent with a friend after a hard day's cycling! Check out RAGBRAI's website for lots of good information. On average a rider spends about $35.00 a day on food but I cut that down to about $20.00 a day by taking along energy bars. I also got off to an early start every day, usually 5:30 am, so that I could arrive at the overnight town by 11:00 am and thus avoid the afternoon heat and humidity. Also gave me plenty of time to just relax and enjoy what every overnight town offered. The people are great and the whole state embraces RAGBRAI. Everything is very well organized. Good luck!