rocksolidsr : I don't see why not - If you have an Arduino that has a removable IC you can pull the IC so you can use the onboard USB-serial adapter to program the Oak. And if it doesn't have a removable IC, you may be able to simply wire it so it is held in a reset state so it doesn't interfere in the update process by responding to something it shouldn't.
Serial port setting would be that of the Arduino. The erase flash setting must be reasonably new, haven't updated the ESP8266 core in a while so haven't seen it before. [Edit: Or I simply hadn't seen it... just loaded the Arduino IDE to check it and that option was there. :-O ] For the first flash, I'd probably erase everything, as the initial OTA enabled sketch you load can be written in a way that it configure the wifi settings itself.
Consider getting a USB to UART adapter anyway - they're cheap as chips, and make life a lot easier down the path as you can just plug in and see any debug messages you have running. Most CH340 adapters are both 3.3v and 5v ready, and are compatible with pretty much any OS.