Every respectable ESP32 dev-board with an on-board USB-UART converter has the auto-reset and auto-program circuit on-board (Using a ESP32 card made by a particular in PatformIO IDE - #6 by maxgerhardt), you shouldn’t ever need to press a button.
Sometimes there are caveats regarding this – see A fatal error occurred: Failed to connect to ESP32 - Voltlog #357 - YouTube.