How do you select the Oak on particle.io? (honest question - wondering if I missed something there??). However, AFAIK, you have to use the OakCLI to switch between the oaks, because the local config.json file stores the device ID of the Oak to be programmed. So if you don't change that value using the OakCLI, or manually editing/swapping that file, you will keep uploading to the same Oak, regardless of what you do on the Particle cloud (when uploading via the Arduino IDE).