There may be factors besides the ampacity, resistance or impedance per foot for choosing a particular size of cable. Some of the factors could be standard cord grip range, common hand tool range, termination type/range at device, size range on intermediate plugs/pins, skill of people installing/repairing, minimize stocked cable types, what type the local distributor stocks, what the regional warehouse stocks, what types/sizes are available with UV resistant outer jackets, quality of shielding, resistance to ground and cost.
But if none of the real life factors are a concern you should be able to calculate the maximum operating distance if you know the resistance per foot, output impedance, input impedance and required range of input. I am guessing your frequency will not be a factor.
Barry1961