1. Glide/Squirrel Nut Butter - As the miles increase so will your risk of chafing. I even put Glide on my feet to prevent
2. Nipple protection - MEN! There are "nip guards" or use a 1 inch flexible/fabric band aids cut in half. (Ask Kim - he's an expert)
Clothing - Wearing new clothes for long runs that you haven't tested out on a shorter run could be dangerous. There could be a seam or something that you didn't realize would bother you and lead to chafing.
socks - Look for socks made of synthetic fiber (not cotton). These fibers wick moisture away from your feet. Running socks are anatomically shaped, helping prevent the sock from bunching up and causing blisters. My favorite socks
are the Balega.
5. Shoe assessment - Have you reached 300 miles yet? Make sure your not running in your old shoes. You've come this long, you don't want an injury you could have prevented.