Trail names usually come from the trail. They should be organic and spontaneous. I took my son out for a hike with a friend of mine who eats nasty, past-their-expiration MREs. I said to my friend, "How do you eat that crap that has far exceeded its shelf life?"
My son said, "What is shelf life?" And a trail name was born - my son's trail name is Shelf Life. It's a great trail name, shared by one of Zippy the Pinhead's best friends.
My friend's trail name (selected by me) is KYBob. He couldn't for the life of him figure out how to milk the bury on a whoopie sling - until he tried KY Jelly to make it more slippery. He is now KYBob.