One option that might work is to symlink the ~/RetroPie/roms directory to the usb drive’s roms directory.
something like:
$ sudo rm -rf ~/RetroPie/roms
$ ln -s /media/usb/roms ~/RetroPie/roms
There is also a USB ROM service under in the setup script
sudo ~/RetroPie-Setup/retropie_setup.sh
Under setup you’ll see the option. This appears to install a hook into the usbmount service so that when you plug in a usb drive it attempts to sync that with your local roms directory. I haven’t used it so don’t know how well it works and it isn’t quite what you wanted.