Looks ok except for VDD -> 5V. The ESP-Prog does not provide sufficient power to also feed the ESP32. It will become unreliable as it crashes when it gets insufficient power during spikes of power consumption.
Can you try a minimalistic platformio.ini:
[env:esp32dev]
platform = espressif32
board = esp32dev
framework = arduino
upload_protocol = esp-prog
debug_tool = esp-prog
debug_init_break = tbreak setup
You won’t see any serial output. And do not use the serial monitor. It’s just for isolating the problem.