How do I automatically sync custom music between macs?

[eseerc]

USE CASE
I have a Macbook Pro and iMac. I regularly cut my own music mixes and have an iTunes match subscription. When I import a cut piece of music into iTunes on my Macbook, It shows on my iMac like one would normally expect. However, I would like to have the music automatically download onto the iMac as well instead of showing up with the little cloud icon to download manually.

Music I purchase will download and sync to both devices, but I am unable to get the custom mixes to behave the same way. How can I get this to work?

 

[Rob Phillips]

I don't think there's a way to have music purchased outside of iTunes automatically download onto your other computers/devices.

 

[eseerc]

Thats what I was afraid of.

I think my next step will be moving my iTunes music into the iCloud drive folder. If I point the iTunes library to that same folder on both machines, i would think that would do the trick?