[kerbobotat]

Does it need to expend the energy to winch it up? Would it not be simpler to have a set of these weights, and a ramp system to deliver them to the top, and use vehicles to unload at the base and drive them back to the top to be hooked up again in sequence? Surely there would be less energy loss moving it up a ramp than fighting gravity in a vertical shaft to winch it directly upwards.

[JBorrow]

No, gravitational potential energy is linearly proportional to the height over which you raise the weight.

http://hyperphysics.phy-astr.gsu.edu/hbase/gpot.html