An interesting way of looking at it. But you're absolutely right: if the gearbox remained cool enough when driving up the hill (overcoming friction and air resistance and increasing the car's potential energy) then less energy will be dissipated in it coming down: friction and air resistance will be about the same, but some energy is being dissipated in the brakes and not in the transmission.
I presume that the oil pumps that circulate the hot oil to oil coolers in the transmission work even when the gearbox is in overrun, with wheels driving the engine which is running with no fuel input - it's not like the problem with 2-stroke engines where the engine got bugger-all oil on overrun because there is little fuel (and oil) entering the crankcase when your foot is on the brake rather than accelerator.
I presume 2-stroke cars, which had a freewheel to prevent overrun from driving the engine fast in a low gear, needed higher-spec brakes because even when going down a long steep hill (such as the one near Lynton/Lymouth in Devon) there is *only* the brakes and no engine braking to dissipate the potential energy lost as the car goes down hill.