Anyone trying to watch YouTube videos getting an “If playback doesn’t begin shortly, try restarting your device” error in Chromium browser can try switching their audio device.
In my case I have HDMI monitor connected and speakers connected to the audio output of said monitor. However the audio of the PI-TOP OS was configured to the AV Jack. Switching that to the HDMI port corrected the issue.
You change the audio output by right-clicking on the speaker icon in the bottom right corner of the screen.