Found that it was Virtual Audio Cable acting up all along. And there's a better alternative available for me built into my computer.
While rummaging through the Recording devices available on my computer, I found this gem:

Check "Show Disabled Devices" and "Show Disconnected Devices" and you just may see a recording device called "Stereo Mix" pop up. This recording device duplicates whatever you send to the sound card's main output. So if you have a second sound device, like a USB DAC, you can simply play sound to your sound card and use "Stereo Mix" as the input device in VSTHost and output to your second device. No need for Virtual Audio Cable!