I like both the PI shorts you've listed. Yes, shorts are critical to your happiness. I also like Castelli.

I agree on Chamois Butt'r. I don't usually use it under 50 or so miles, but if I doing many continuous days of training I may use it every time. Do whatever works for you.

Food and Gatorade -- whatever works, you're willing to eat and can digest. You may want to do a little comparison of energy drinks for the types of sugars and electrolytes. As the weather gets hot you may find that youi want to switch drinks and/or food for digestibility or just because somethings taste better.

I'll be keeping on eye on the Rx glasses question because Bubba wants some also and we need to figure out what to get.