Ok, I need help from you long distance guys here, as this is something that really in not a problem for me in shorter stuff.

I did Gulf Coast this past weekend, and ran in severe pain from about the 5 mile mark on, resulting in a unspectacular 1:37 run split for 13.1. I ran in my Nike trainers, rather than in race flats, and wore Jox Sox(socks). This combination became immediatly soaked from the water from sprinklers, sponges, etc, and blisters formed quickly. Then I could feel the blood blisters under my toenails(black toes) forming. I know that this slowed me down, as each step was hell.....though I never walked, and cost me from going under 4:30(my goal). Any Ideas? Is there a shoes that drains better? Could I drill holes and create drainage? Better socks?