My experience: I'm used to older systems where you can overcharge the system (not great), and I had done a non-Jeep and the system would detect the overcharge and stop the compressor. Made the vehicle drive poorly too, as the compressor would kick in and out. Solution was to let a little refrigerant out and normal operation ensued.
I believe I had similar with my 2013 GC V6. The modern systems are picky as to how much you can put in.
(Also, running the system a bit will disperse the refrigerant and the oil charge. This can solve itself in short time. This might be the source of the whistling after shutdown)
If you're getting cold air, that's a positive sign. If the compressor is cycling, then you have an issue: too much or too little charge. Putting the gauge on the port can tell you if you're getting too much.
Note: A/C works by exploiting the energy required to make a phase change, from liquid to gas and back again. You can't get a good reading without the compressor running: having a minimum amount of Freon in the system with vehicle off can read as a high pressure, same as having a full charge or more (same is true on a propane gas grill cylinder: the pressure just tells you gas is present, and it can't really tell you the fill level until you're at the end of the tank). A compressor that is able to run continuously with the engine speed around 1500 - 2000 RPM is an excellent indication that the fill level is correct.
When the compressor is running, ideally there is a high pressure side and a low pressure 'suction' side. When you turn off the motor, these different pressures will equalize: this is the hiss you're getting. If the valve that regulates the pressure is obstructed, it could be the source of the sound, and I'd hope that it'll clean itself out in short time.