Check the outlet temp at one of the vents when this is happening. Units that are low on refrigerant will tend to freeze the evap and blow a white vapor from the vents. You can also check the accumulator to see if it is icing up along with the lines.
for that to happen he would have to also have a failed LPS (low pressure switch) this would allow the compressor to suck enough refrigerant out of the evap to cause the temperature to drop below freezing.
you can't charge by pressure when the ambient temp is below 75 and not at all when it's below 60. if you can get a set of gauges get them on when it's warm out and watch the low side pressure. shouldn't be too far past 50 (high) or lower than 25 or so without cycling the compressor. the service dvd says The electrical switch contacts open when the suction pressure drops to 152-193 kPa (22-28 psi).
The contacts close when the suction pressure rises to 276-324 kPa (40-47 psi).
if your system is under what I would call a "nominal" load, you should expect the low side pressure to be close to the cut off point of that switch when you have the engine at 2k revs. high side should not be much higher if at all, than 250, the high side safety switch operates at 420 psi and closes again at 250 psi. this one will open at idle if you have a bad clutch fan. ( mine does, simple test is if it starts to cool again when moving faster than 20 mpg)
all in all, I can speculate all day what's wrong but it's useless without pressure readings. I will also need to know within 3deg the ambient temperature of the outside and inside air to see if the pressure you have is okay