My unscientific impression thus far is that in mixed city/suburban driving where the speed never exceeds 50 mph, the S consumes about 285-290 Wh/mile, on average, which means that the actual range will exceed the rated range by a few percent. I'm pretty good about staying off the binders, but the seat of my pants is still tuned to the Roadster's stronger regen braking, so I generally do have to use the friction brakes a little more than I'd like. Still, the stop-and-go range seems pretty impressive.
Started the day with ~240 and gave a few test drives to some friends; it was as I parked at lunchtime that I noticed this:
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Note that Sarasota is flat as a pancake (this isn't from running downhill at all). This comes from driving around the city and coasting with regen up to stop lights. I always have good city mileage in my Roadster, despite showing off when the lights turn green.