Headless Mac mini as iTunes server

Yeah, it's frustrating. You can disable the software updates from Preferences > Advanced. It won't fix other issues, though.

 

Can you take the headless mini back to an earlier OS and an earlier iTunes?
You'll get fewer annoying messages.
Keeping your iTunes signed out and off the internet is also helpful.
This AppleScript is good for closing unwanted dialog boxes:

Code:

tell application "System Events"
    try
        set z to name of front window of application process "iTunes" -- <-- It's NOT "myTunes" here That doesn't exist.
        -- This returns "" if it's a warning dialog
        -- "iTunes" if it's the main music window or mini player
        -- Track and album name if it's cover view up front
        -- error if no iTunes windows are open
        -- "General Preferences" if Prefs is open
        -- Album name if "Get info" is open
        -- "Equalizer" if equalizer window is open
    on error
        set z to "Bubblepuppy"
    end try
    if z is equal to "" then
        --set z to name of (static text of window 1 of application process "iTunes") as text -- might eventually be useful
        delay 0.1 -- iTunes needs a little time to stabilize
        keystroke "
"
    end if
end tell

Put it in the iTunes Script folder and assign a key shortcut to it, so you can trigger it from your iPad.

 

I used a 2012 base mini (2.5ghz/4gb/500gb HD) with my library on a 3tb external USB 3.0 disk as an iTunes server for two and a half years. I used the original Mavericks and whatever version of iTunes was pre-installed the whole time. It was set to never sleep and never spin down the external drive. After several months uptime there would usually be some odd glitch, but a restart always fixed it. So I consider that very robust, it probably needed restarting 4 or 5 times per year. I don't ever recall a dialog box causing iTunes to stop sharing.

I wanted to use the 2012 Mini for something else, so last summer I replaced it with a base 2014 mini (1.4ghz/4gb/500gb HD) that had El Capitan pre-installed. My experience has been the same with this machine, it is very stable with even longer uptimes than the 2012. Now the only difference here is that mine has a "head". I used my ancient 12 year old 720p Samsung LCD TV on the 2012 machine, the new mini has a cheap new Samsung 720p LCD TV.

I did have to spend more time turning things off on El Capitan than I did on Mavericks. Am still getting calendar updates there so I must have missed something, but they don't have any effect on iTunes sharing.

 

That's unfortunate you are having those issues, I'm running the same setup, 2012 mini on the latest macOS, and experience 99% or better uptime of my iTunes sharing. I also use the remote app and route output via airplay. With maybe 3 to 4 incidents a year requiring intervention to restore the service. I can't even recall the last time it was down, it's been a while.

I can only wonder as to the types of errors and events generating the interruptions. What sort of errors? What sort of reoccurring events? Tracing those isssues may hopefully mitigate the problems that keep causing the interruptions.

Some tips to make it work more smoothly?

If not already doing so, use a headless plug in the HDMI port. It causes the accelerated graphics to initiate, improves overall graphics and screen sharing performance. This one works well for me: https://www.amazon.com/gp/product/B00FLZXGJ6/ref=oh_aui_detailpage_o01_s00?ie=UTF8&psc=1

At least to simplify maintenance access, get a VNC app for your iPad. No more booting other computers to screen share into the mini. I recommend "Mocha VNC", it works well with the MacOS screen sharing protocol, been using it since the dawn of the iPad.

In addition to sharing from iTunes, I also use a second service to stream media, ServeToMe. It let's me stream the iTunes library independent of iTunes, and I use it for client side access to stream my home library to iOS devices, locally in the house and even remotely over the internet.

So iTunes provides the local system for sharing (homeshare and bonjour) to home media nodes: Apple TVs, computers, airport expreses. The ServeToMe gives me local and remote streaming direct to client devices: iPhone, iPads, etc. The client side app is called StreamToMe.