2003 Chevy Monte Carlo Climate Control Not Functioning

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First off, does your SS have the automatic A/C system or the manual A/C system? A/C systems usually require certified HVAC techs to repair them as it takes many specialty tools to diagnose A/C issues..There could be restrictions in the system somewhere such as restricted condenser air flow.

Well Im not sure what type of system it would have really. Theres a fan level switch, 2 temperature switches 1 for each side, then the switch for where the air is directed. It seems like a pretty normal/simple system. I actually vacuumed it out one more time since I posted this question and it did get colder, not as cold as a freshly charged system might get, but colder than its ever been. I am experienced in changing out freon and reseting the system, and have all my gauges, manifold gauge set, vacuum, etc..., just have never dealt with a dual climate control and especially a problem where one side is colder than the other.

normally the dual a/c systems are auto..in any case, when dual a/c systems get low on refrigerant the driver side tends to stay cooler than passenger. if the refrigerant was low then there is a leak in the system somewhere because a/c refrigerant should never leak. then again it may not even be a/c related. it could be caused by a leaky cylinder head gasket. does the engine temp. seem to run normal? make sure coolant level is full as well.

Yes actually, just about 2 weeks ago 2 elbows that come from the belt tensioner to the head busted. Common in this type of engine. Car started overheating but ever since I replace those elbows and flushed the system, put a cooler thermostat in, It runs at about 180, or below half. Doesnt seem to be a leak either the manifold gauges read that it held 29 Hg pressure for 30 mins. Could it be just that I have to reflush till it becomes coldest.

Also one thing Ive noticed is the a/c low side lines and condenser are very close to the headers, which dont seem to have much of a heat shield. My engine bay gets very hot, although it is at a normal internal temperature. Could this be causing it.

not sure if reflushing will help but since you said it did get it cooler than its worth a shot again. if it doesn't help, there maybe an issue with the actuator that is not opening one side properly allowing some warm air to blend with that side's cold air.

you may want to add some insulator around that area to see if it helps, it is a cheap fix and wouldn't hurt anyway.

This isnt the first time Ive heard about the actuator malfunctioning. It seems like this would be the highest possibility. Where is it and how would I check it?

check out the drive shaft of the left and right air temp. actuators. place the air temp. switch from the coldest position to the warmest position and watch to see if the drive shaft of the actuator rotates. there are 2 actuators, left and right side behind the instrument panels/dash, attached to the heater-a/c assembly.