After DJI Assistant two is up and running and your drone and controller are running and connected, then plug the micro usb to your drone and the usb to your computer. If you’re using a Mac, most likely it will connect right away. I had some issues getting my Windows based PC to recognize my Mavic (wish I had documented the fix).
In summary, it’s my understanding that once you’re connected to the drone through DJI Assistant 2, that’s all that required to keep your total system up to date.
I tried what you mentioned, attaching the remote to my PC, but it only charged the remote, no hand shake or data transfer.
May not be totally accurate but I hope it helps some