did you try make clean ?

The following scope capture shows the 3V3 rail and the voltage on EN line : (Green = GPIO34 / Yellow = 3V3)

This statement is confusing. Is the scope capture for the green line showing the EN line, or GPIO34 ?

What I have done which helped me was once OTA has been started, I kill all tasks that I have created. In doing so give full CPU resourced for it to handle the OTA update.

Also, why use 2 IO pins when you can use one to do the same thing. Tie REED_NC to +3.3v, and tie REED_NO to GND. From the Com. side of the reed (the side you have going to 10k then to +3.3v) take that to your input pin. Good suggestion, but considering that the reed switch will always be positioned...

From your schematic, this is not how you want to wire up your pull up resistor. Doing it this way can cause the pins to pick up stray interference because they are floating. Also, why use 2 IO pins when you can use one to do the same thing. Tie REED_NC to +3.3v, and tie REED_NO to GND. From the Com....

Check out ESP-ADF. (Espressif Audio Development Framework)

https://github.com/espressif/esp-adf

Thanks, however there is no way i can tell by the photo. Does your button have a pullup resistor? It does not look like it.,

How is your button wired up ?

Just put a 6 pin header on your board and buy one of these. It will do what you want.
https://www.gridconnect.com/products/es ... gging-tool

How did you get platformio to work with ESP-IDF v3.3 ? They are not on that version yet.
platformio is a good solution. Though the biggest problem i see with it is that they dont support menuconfig.