Hopefully I didn't make my title too long, but anyways I am looking for a way to route my audio output (that would normally go to my headset), to essentially my mic input while allowing me to still listen to my output and use my mic to contribute to the input. (Pretty much not interfering with my use of it.), sort of like achievable with Virtual Audio Cable on windows.
Also, I am looking for a way to turn off this with a hotkey;
I am not blindly asking, I have dabbled with Jack Audio Connect Kit and qjackctl and had my errors (couldn't connect to jack server) that I have supposedly fixed. However my "fix" doesn't allow me to pipe the audio through, as well as I can't hear or input anything.. I am very new to all of this audio stuff, and not as "intimate" as I would like to be with linux, and I am rather newish (about a year.. not quite a newbie, but I am still new on the deeper stuff in Linux.) so more of less a tutorial would be appreciated, by any feedback will be helpful.

Of the stuff recommended on the 'net jackaudio is the only one that's not deprecated like http://www.vsound.org/ or part of a software suite like http://kxstudio.linuxaudio.org/Applications:Carla. So if you never troubleshooted your jackaudio adventures on LQ, maybe give that a shot?

This is not a field I'm familiar with, but I do know Jack's the tool:
https://help.ubuntu.com/community/What%20is%20JACK
http://www.jackaudio.org/