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Hi I'm Brian and I'll be happy to help you figure this out!
On the first question: It's not possible for a unit to be low on refrigerant unless some has leaked out or been taken out. Refrigerant is not consumed in any way shape or form in an ac unit.
With that said, it sounds like you have a different problem although you should have the refrigerant level checked. With a system of that age, the first thing I would do is look carefully at and thoroughly clean both the evaporator (cooling) coil and the outdoor unit coil (condenser coil). I would also check the indoor blower wheel and housing for accumulated dust and dirt and clean if necessary. Then after the outdoor coil dried, I would check the refrigerant level.
With a leaving temperature so low on a warm start up, this really points more toward a clogged (dirty) evaporator coil (indoor coil) or a dirty blower wheel. Either of these conditions cause low airflow and low supply air temperature. It can also cause ice-ups. You can't really tell if your refrigerant level is correct unless both coils and the blower wheel are clean/cleaned.
Let me know if you have questions about this.
Ok thanks for the added info. If you still have a gas furnace then yes, the cooling coil would be above the gas furnace and many times they are insulated on the exterior. Newer coils for gas furnaces are encased in a factory sheet metal enclosure and insulated on the inside of the enclosure but many older ones were insulated on the exterior. That's unfortunate you can't gain access to the cooling coil, chances are after 16 years it has accumulated a lot of dust and is likely pretty dirty. A qualified and quality technician should be able to gain access to it to check it/clean it.
Yeah, with that temperature coming out of the vent, I would bet you don't have proper airflow for one of the reasons above. It sounds like your furnace and cooling coil need a really thorough cleaning! Then the refrigerant level can be checked and perhaps it may be a little low. Tiny leaks at gauge port caps are common so it could be slightly low on refrigerant as well as in need of cleaning.
Sorry, I"m not a very fast typist ;)
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