I have a chromebook that doesn't have video-out ports, but a relatively basic USB-C hub with HDMI-out port sufficed to get it connected to my HDMI monitor. Not sure if that's a counter-example, or something else entirely, but it may be relevant either way...
That Plugable adapter is interesting -- the page doesn't claim it's an "active adapter", and it only costs $15. In my mind, "active adapter" always translated to "costs $50 or more".