ccbloom--You're not alone in stressing over road riding. My college campus is smack in the middle of Cleveland and is near a hospital, so it's quite busy, especially now that school is back in session. Even though I know drivers around here are used to seeing cyclists, and dumb ones at that, it still makes me nervous. The roads are not always well-maintained, I don't know all the streets... I'm also not from the area, so I don't know bike trails, and I don't have a car to get to them even if I did.
We have a cycling club. It's mostly--if not, entirely--guys who like going way too fast for me. I have learned some good ride routes from them. (I just tell them that I can't make it, but I'd like to know the route.)

I just try to make myself as visible as possible and head out early on weekends when there aren't as many cars or freshmen around (because they haven't figured out how to cross streets yet). There are a few neighborhoods around here that I'd like to ride in. Yes, it involves walking my bike across a couple of intersections to get there, but it beats getting squished!