You'll need a 3v3 USB to serial converter, so make you have one to start with... Something based on a CH340 is good... and ridiculously cheap

At that point, if you just want faster, more reliable uploads, you can upload to the oak over the usb-to-serial link instead of OTA.
If you want OTA, but a bit more reliable, then the Arduino ESP8266 way is probably the way to go. But basically, so you don't burn any bridges, I would first backup the entirely of the Oak's flash memory, so you can re-Oakify it if you wish to at a later date. You then upload a program to it via the USB to serial link when using the
Arduino ESP8266 core... that's basically it (with the oak in flash/programming mode - P2 to GND on power up IIRC). You can also upload their ArduinoOTA sketch, which then gives you OTA programming capability (and scaffold for adding to your own sketches)... which is also much faster than serial uploading... much faster!
Sound like something you want to find about more