Nope, you won't need to pedal to get going, no matter what your winding is.
Plenty of power for steep hills and starts, even with the faster windings.
Uphill starts will still be a place to pedal some to get going, it is after all, only a modest size magnet motor. Especially if you are heavy, you may have some sluggishness if the hill is steep and you are stopped.
Adding more power to this size motor is not particularly good, but 2000w will fly if you want to up the amps to 48v 40 amps.