seeking a better AC…and ideas

[mudgudgeon]

that sounds very interesting...

Won't be needed in Chicago.

Not needed in Australian summers where ambient temps can be 100-120⁰F.

Only time I had issues with my AC in Australia was when the fan clutch on the engine fan was bad.

Search for a thread on "blue fan clutch mod"

 

[Rollinns]

You have issues. This is what my 94 puts out in Florida in May.
View attachment 3626892

That might be ok in Florida where the hot temps keep hot air flowing past the evaporator all the time, but with a register (vent) temperature below 32F, your evaporator may freeze up (which may cause other issues). It looks like your refrigerant is a bit low, normally you want register temperature above 32F, I usually charge mine until the register temperature is between 36F and 45F.