Correct on a Mac I can't run the official software.
Thanks for asking me the basic questions, sometimes I mess up... basically.
Yes, the data cable is in the data port closest to the fan. I am using the correct com port from Chirp. I've even done the "Help Me" in the port drop down and it leads me to USB-Serial Controller. (I've also tried all of the other options.) I have done a factory reset and still have this issue @OffRoaderX.
The sequence is hitting okay to download from the radio, Chirp says "Cloning from Radio", it stops and throws the "Short read of the block 0x000" and then the DB25-G makes a clicking sound and reboots. I do not notice any spikes on the AMP levels on my power supply when this happens.
I'm considering trying to find an older version of Chirp to see if this still happens.
Thanks to everyone for their help!