How do we select multiple songs and add to a device using keyboard

macOS and Mac Apps

Hi friends,

There are two questions I would like to ask here:
1. How do I select multiple songs that non-sequential using VO and keyboard?
2. How do I add those selected songs to an iPhone or iPod.
As of now, I am going down the list of songs; then tabbing tot he Action menu and add each song to the device. But it consumes a long time. Moreover, I am unable to get the context or action menu for each song by pressing CTRL+Option+Command key. I don't know why this happens. But I am just unable to get into the action menu of a song by pressing these key strokes.
Any help is appreciated.
I am using iTunes 12.9.25 on Mac OS Mojave.