Thank you, once again, for your assistance. If I am not understanding your instructions correctly, please let me know.
At no time, during this test, was a usb-c cable attached between the Digirig and a computer.
The Digirig was secured, in a vice, as seen in image named, 1.
I set my multimeter to the settings in image named, 2.
Without any cable, of any kind, attached to the Digirig, when I measured the resistance between the GND and the PTT solder points, without touching anything other than the tip of the probes to those solder points, the multimeter read 0k Ohms.
I then plugged the TRRS end of the cable into the Digirig. The Kenwood-style connector was not attached to the radio. I measured the resistance between the GND and the PTT solder points, without touching anything other than the tip of the probes to those solder points, the multimeter read 0k Ohms.
I then plugged the Kenwood-style connector end of the cable into the radio. The TRRS end of the cable was plugged into the Digirig. I measured the resistance between the GND and the PTT solder points, without touching anything other than the tip of the probes to those solder points, the multimeter read ~68k Ohms. The radio was not powered on.
I then unplugged the Kenwood-style connector end of the cable, turned the radio on and tuned the radio to a NOAA WX Station, at 162.472, and ensured reception. I turned the radio off and plugged the Kenwood-style connector end of the cable back into the radio. The TRRS end of the cable was still plugged into the Digirig.
I turned the radio on and the radio immediately indicated PTT, as seen in the image named, PTT.
Your email mentioned this phrase, “measure the voltage between GND and PTT pins”. I set my multimeter to the settings indicated in the image named, Voltage. I measured the voltage between the GND and the PTT solder points, without touching anything other than the tip of the probes to those solder points, the multimeter read ~3v.
I am more of a musician than an electrician
If I am performing these tests incorrectly, feel free to yell at and correct me. 
This behavior happens with the UV-5r and its cable as well as my ID-52 and its ICom cable.
The photos are in the attached zip file. The first reply I sent was bounced due to size.
Archive.zip
I hope you have a great weekend! Thank you for your help!
Crittenden