Thanks for the responses folks.
To clarify, when I have my unit set up (Laptop---[USB]--->GNX4---[1/4" Headphone jack]--->Headphones)
yes, I can hear computer sounds (Win10 chimes, Facebook Notifications etc) and Cakewalk outputs.
However, if I try and say, listen to an MP3 in Media Player, or Watch A YouTube Video, I get popup messages. Ideally I'd like to be about to seamlessly switch between working in Cakewalk, and referring to instructional videos, testing my mp3 outputs, etc. Currently, to do those things I have to save and close out of cakewalk, and then open it back up. Its not the end of the world, just cumbersome.
On the second note, Switching to WASAPI Shared seems to have made me some progress. I can now set output to my speakers. But do I have to do it on a track by track basis? or is there a quick way to reroute all output to my speakers at once?
Appreciate the assistance.