The PI Attack shorts are my favorites. I have worn them for several centuries and have never had any troubles with comfort or chafing.

I've never found a need to use the chamois butt'r. But, if you find you are getting discomfort or chafing during your training rides, you may want to give it a try. I know quite a few people who swear by it!

For food, I usually carry some energy bars. I've done ok with gels too. Some of my other favorites are peanut butter sandwiches and payday candy bars.