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Yes, video is rather old, but the same methods of linking different programs, ins and outs apply.
Some versions of osx have issues with jack, here it is mentioned and a version that does work
is linked, https://ccrma.stanford.edu/software/jacktrip/osx/index.html
jackctl is whats used in Linux, the name is unimportant, and it was not me who said I did not care.
It is a relatively easy program to use, the video I linked shows the way around it.
First you tell osx to use it as the sound device instead of core audio.
And in the jackctl settings, you can tell it to use 15 chanells, or more if they are available,
these channels can then be used by the programs, so each program uses a different one or two
and not conflict with another program.
Then in every program you want to use with jackctl you find the settings in the program and tell it to use
jackctl.

Most audio programs work with stereo, so channel 1 will be left and 2 will be right on the master,
if you input only on channel 1 you might see only one side of the DAW master meter light up, if so and
you want stereo input the same source to chanel 2, that should solve that problem.
Its just a matter of playing around and building up on how it comes together.

Looking at the image in your first post, it doesn't seem jack is installed, though am not familiar with mac,
the images in the link I posted in this replay are very different.
You also need to install jack first, then whatever jackCtl you are advised to use.