Experience is where it's at - just spend time on the road, the more time on the road, the more comfort you'll have in the street, and the more comfort/confidence you'll have riding around/close to cars.

I don't usually run reds often, as noted above the fine here in Toronto is pretty hefty, and frankly, I'm just not in that much of a hurry - I like the interval training.

That being said, if I'm in an alleycat, I'll take a lot more liberties - that's a confidence that's still growing and I'm still learning - knowing the city helps I would guess, I've never been to NYC, but I know from riding here in Toronto that there are some major intersections I wouldn't think about barrelling across, and some that are pretty tame - knowing when you can/can't take those leaps of faith is important.

Ride carefully, build your confidence - in this case it's best to go slow and work up to it rather than go all out and bust... the "bust" might just be your head/spine against that cold cold steel of a motor vehicle, and then you won't think it's so cool to be thrashing about on the roads.

oh, yeah - life sucks: get a f*&^ing helmet!