[turtle]

Thank you chucker! I just might be able to work through something like this. I did create a calendar event with Automator but it expects that the iTunes is set to Airplay. I don't have a dedicated Mac configured for it so that is a challenge at the moment.

At this point it looks like I'm going to be able to cobble something together though.

I have another challenge that I've hit my computer limits with iTunes and family sharing. So I'll end up building a VM that is standalone on the network just to play locally stored songs. Seems overkill to do, but it would allow me to manage via Remote Desktop and still script it out. On the plus side, it won't effect my play count out those songs since they are background and I really don't want to know how many thousands of times those songs will play. The real downside to this is that I'll have to manually copy songs over to the VM and import them in rather than manage the playlist on any of the connected iTunes Macs.

Yontsey, thanks for the tip on Sonos. I might just go that direction for my home audio anyway as a general play. I'm not interested in Alex, Google Assistant etc... listening in my house all the time. That at least saves me a little money in buying new speakers for the house.