The Tesla EPA estimated range values for the Tesla vehicles are for a combination of city and highway driving. (The Tesla EPA range values are derived from Tesla battery run down dynamometer (dyno) driving simulation test results, not actual street driving.)
City driving can be more efficient than highway driving due to the lower speeds of city driving. Regenerative braking can recover perhaps 70% of the energy that would lost using friction braking. Regenerative braking does extend range by ~20% in real world driving conditions. When you drive up a hill then you can recover a significant portion of the energy used to lift the weight of the vehicle to the top of the hill (or mountain) when you descend but you cannot recover more energy than you consumed through regenerative braking (unless you start your trip at the top of the mountain.)
Regenerative braking can recover some of the energy that was used to accelerate the vehicle from a stop up to the cruising speed. The time and miles covered while at the cruising speed is not a factor when recovering energy through regenerative braking. When slowing the vehicle using regenerative braking instead of converting the energy contained in the forward momentum of the vehicle into heat (this is what friction brakes do) some of the energy can be recovered and put back into the battery.
Regenerative braking can never recover all of this energy due to inefficiencies when converting mechanical energy into electrical energy. For this reason coasting, rolling in Neutral, to slow and finally stop the vehicle is more efficient than regenerative braking. However, coasting is neither safe or practical when driving on public roads.