edit: see next post
You have waveforms showing 2.74v pk-pk at pin 6 and only 320mV pk-pk at the cathode of C309. The ohms look right on that side of the cap, so IMO, it can only be a couple things. 1, C309 is dry, but you said you changed all caps, so I doubt it. 2, those diodes are conducting well below 0.7v, but everything I find online suggests silicon, so that doesn't seem right either. 3, maybe the 320mV pk-pk is a false reading taken during a low in your voice and I am focused on the wrong area ~ one of the reasons to inject a constant tone when looking at signal levels.
I would start with eliminating the mic and injecting a steady 1kHz tone at 30mV pk-pk and get new waveform screenshots around those same points.
I have this modeled in LTSpice and can share the file when I get home if you want to mess with it. My model shows roughly the same pk-pk on pin 6 and the other side of C309.
I have a radio with a similar circuit, a midland 13-892, but I need to recap and align it before I can use it as a waveform reference. Not sure I will have time to go through it this week.