Keep the redline low so that you are always in the flat torque region? Would have to be a torque monster like you say, for that gearing.
The best way to think about the Roadster torque curve is that it has three parts: the flat region, which is limited by the motor; the linearly declining region, which is limited by the input power (the ESS), and then the superlinearly declining region which I think is also related to motor performance at very high RPM. Because the linear region is related to the battery, nothing you can do later in the powertrain will make it better, though you can make it worse. So, if you were to increase the gearing the in the Roadster, you would be in the flat region longer, but only because you're delivering lower overall torque, so it hits the power limit later. That is, it would be a strict loser in terms of 0-60 time.
The way to think of the gearing tradeoff is that lower gearing means greater low-end torque, faster 0-60 times, an earlier start to the linear region and lower top speed. Higher gearing is the opposite. Since top speed probably isn't that big of a concern in the Model S, I wonder why (if) they really went to higher gearing.