I've resorted to using serial to flash the Oaks I have, Particle is proving to be erratic with OTA updates.
The method I use is to hold digital pin 2 low and then reset the Oak, then release digital pin 2 after 2-3 seconds. The Arduino IDE can then flash the program to the Oak over serial.
I have occasionally (twice during 7 days of intensive programming/flashing) had this fail but I just restored the V1 firmware and everything sprang back to life.
Serial programming might not be as convenient but during development I'd rather just have something that works "every" time than spend time trying to flash, fail, flash, fail and then resort to using serial anyway.
Hope this help,
Mark