I have the same issues. Once I'm awake, I usually have to stay awake for at least a couple hours before I can fall back to sleep. And in order to fall asleep at night, I have to let my mind wander.

I've read a lot of techniques involving concentration exercises like counting and saying "I'm dreaming" until you fall asleep or visualizing, etc. I don't know how people do it. I just end up counting for hours with my eyes closed and as soon as I stop counting, I drift off.

I recently bought a program that makes brainwave entrainment CD's which work without headphones. I'm planning to test them out with WBTB and WILD soon. Hopefully, they'll at least help me fall back to sleep faster and maybe even manage my first WILD...