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So it's a pretty drastic jump in a/c temps when the outside temp may just go up to 85ish. See, that tells me it's something like the low pressure switch on the a/c, or even something with the controls or actuator doors. If the a/c works at 80 degrees out, but not at 85-90, I don't think it's the fan or evaporator. Something is telling the a/c to stop working correctly when the outside temp is warmer. Just for kicks, have you tried changing the vent when it's 85+ out and see what happens? Meaning, turn on the a/c and switch the vent to defrost, or to your feet, or anything and see if it changes anything? Do you have rear a/c? How is that affected?
The actuator doors I'm talking about are the ones that control where the blower air is coming from. Does it flow over the cold a/c coils, does it flow over the warm heater coils or neither. If the controls aren't working, or the actuator doors are binding, or anything like that, the a/c might be working fine but the air just may not be blowing over the right set of coils. Is it the automatic climate control system or do you manually turn the dial to warm or cold? Check the rear air, that might help to figure out what's happening. If the rear air works fine, then it's probably something in your control system or blending doors. If the rear air doesn't work, then it's something else.
Sunlitcomet is right about that. A good set of high/low gauges should be able to tell you what's going on. Didn't you say you took it to a shop? I'd take it somewhere else. I know lots of places around here will hook it up and check it for free. That would at least tell you if you have a clogged orifice or somewhere else, or if your compressor is weak. Take his advice!!
Did you ever check the rear air or try turning it to defrost or the foot registers and see what happens?