While trying to program the ESP32 I found a few big mistakes in my PCB. Firstly I forgot to route the Enable Pin. thankfully I can easily solder a wire to it. I also made another mistake with Pin 2. During programming Pin 2 has to be held low or floating. I had it pulled high and used as the PTT for the Input radio. Thankfully this is an easy fix on the current board of just cutting its trace.
I haven't found any additional issues and will be trying to get it working over the course of the week.