Cool ESC first then motor as my usual way. Because motor price is cheaper than ESC
I think the main reason is that the temperature of ESC is lower than the motor. First cool the ESC and the water will become higer but still lower than the temperature of the moter, so cooling effect still could be achieved. If we cool the motor first, then the temperature of the water may be higher, then the cooling effect to the ESC will be minimized or even there is no effect.