I live in a downtown that is fairly well lit and later at night is double the width as no cars are parked anymore. Since last July, I've gone up and down these streets thousands of times, literally. I skate it January and in June and know the topography to the point I could shut one eye and do fine. In Mass, there are potholes and rocky roads everywhere so you get a sixth sense for your terrain. It's like when a sandbar moves from a storm and starts pumping again - when the streetsweepers hit you have a whole new set of waves that were covered up prior or at least you couldn't get the same speed leading up to because of sand or rocks. After skating these roads in fall and winter rain, snow and rubbish, summer pave is like surfing perpetual glass.
I've night skated in so many cities and on so many roads I'm quick to absorb the surroundings. I have tunes cranked to da max on the phones and that's fine because it's all visual for outside elements. Drivers are such kooks that if you're going on the sound of them it's probably too late. Plus, light travels faster than sound and I can see headlights well before I could hear any oncoming cars.
My town is pretty dope for inclines/declines so it's got a lot to offer. In one square mile I'd say there's 50-60 asphalt waves breaking good to great that are ready to be hacked to pieces.
Always check your equipment before going out for a rip, especially when hitting speed and/or hills/pools. Always have a pair of skate kicks that you don't wear out otherwise so they have superior grip. Always have the fattest beats in those phones so you can sculpt your style and I highly suggest playing sick tunes that you saw someone crush lines to in a nasty skate vid. Puts you in the scene yourself. And always, always rock shades from dawn til dusk, if for nothing other than style. Amber lenses suggested. If you've got the whole visual absorption thing down then you're set.
Lastly, don't try any of this at home because none of you have more than nine lives like Spicoli and I should've been deader than the Ghost of SJB back in the 90s. Just hasn't happened so I rock on with no relent.