I hate you just hearing you describe it.
My problem is that if I stay up, I won't get tired until 1:00 or 3:00. (I should be in bed by 10:00 to get 8 hours of sleep.) If I go to bed when I'm not tired, I'll lay awake until 4:00 or 5:00. I'm not overly stressed, I just think too much. I start thinking about how to fix things, things I need to work on, future projects, etc... My brain really hits its peak at night and I have trouble shutting it down. Having the TV on helps distract me and helps my brain shut down for the night. The more mindless the better. Robot Chicken and Aqua Teen Hunger Force work really well, as do some boring History Channel documentaries (but these are becomming rarer). The plus side of this is that I can easily stay awake for 24 - 36 hours before getting tired, provided I actually got sleep the night before.
When I wake up in the morning, I don't want to be awake. I rarely start my day ready to go. I usually crawl into the shower/bath, lay down, and sleep for another 10-30 minutes in the shower in the morning with the water running. I've even fallen asleep sitting or standing up in the shower. I'm that tired every morning. It takes a good 2-3 hours for my brain to get going in the morning. I don't talk to ANYONE the first hour I'm at work, and everyone knows better than to talk to me.
Taking Melatonin has made the falling asleep easier. I'm usually out between 10:30 and 11:30 now. I still have trouble waking up in the morning, but it's better in that I usually have one morning a month where I wake up ready to go. (Previously it was one morning every six months.)
I don't remember having problems sleeping in high school, but I remember when I got to college all of the noise in the dorms kept me awake. I started keeping a fan running and the TV on to drown out the noise. Now I CAN'T fall asleep without background noise. My first few years in college, I did't start class until 9:00 or 11:00, so my natural rhythm of falling asleep between 1:00 and 3:00 didn't deprive me of any sleep. My senior year I worked mornings off campus from 7-12. I took to using a thing widely available on college campuses to help me fall asleep, but I soon got a job offer and had to quit that too. I've been sleep-deprived ever since.