Enthusiasm - not all bad.
Anyways, I've tested much more extensively and the above code *does* work, and my Oaks seem fine. The problem is one of flashing an Oak when connected to other hardware.
Observations:
1. Oak (often/usually) does not go into flashing mode if connected to a powered SD card board, with card inserted. These suck a great deal of power at startup; a documented problem with 5V Arduinos and presumably more of a problem with a 3.3V MCU. New SD cards especially are problematic. Possible solution: add a delay(2000) in setup to give time to either start a flash, or connect the power pin or push the SD card in all the way immediately after the Oak powers up
2. If connected to an SPI board, i.e. TFT screen, audio/amp board, etc., and the active sketch interfaces with these, an OTA flash often does not work. Shorting pin 1 to trigger Config Mode then does allow it to flash - usually
3. If step 2 fails, it will usually succeed if trying a few more times. If it doesn't, disconnect the SPI board and try again. Once the sketch uploads correctly, reconnect
I've tested the SD to SPIFFS code with as many as 8 files at once, as many as 612,080 bytes transferred to SPIFFS at once, and have verified that all files transferred cleanly. Additionally, the Oaks appear to be working properly, but will continue to test