Adding movies to Kodi

Tried to find the solution but didn’t see it so sorry if I duplicate. I just set up Kodi on a Pi3. I have a USB HDD attached to it that holds my movies. If I get a new movie, how can I remotely get it over there? Thus far I’ve had to:

  • Take the USB drive to my computer
  • Copy the movie to the USB
  • Plug it back into the Pi
  • Connect a keyboard to the Pi
  • Navigate to Update Media Library and update it

Is there any way to do this from my desktop? As this is still new, I am adding LOTS of new material all the time, I can’t do that all day.