Why original music won't play (greyed out) ?

I know this is a well covered issue with Apple, iTunes, iPhones/Pads/Pods... I'm reading tons of questions and different solutions about this problem.
I had my share of this with purchased music as well as CD copied. My ecosystem is all Apple (Apple desktop, MacBook Pro, iPhones, iPads, Apple TV... My loyalty is (still) there as I have invested too much in iTunes purchases :-) ...
But I also need to use all this ecosystem as a work tool and 2 times out of 3 (can't figure out why it works sometimes...), when I create music and need as a producer to test some mixes in my car or earbuds through an iPhone, I'm stucked with a file that remains greyed out on some devices, even though it will play on the computer where it was created.  The song title appear on my iPhone, and on MacBook Pro but remain greyed out.  No cloud image on this line that I could simply click to bring it on the device.
No I have not unplugged anything.
Yes I use sharing and I subscribe to iMatch which should make everything available everywhere...
Even a forced sync (wired) won't fix it. And no I don't want to backup, reset, spend hours to this bug which appears to last forever from posts I am reading back to 2010 and probably earlier, which should have been fixed by Apple for long... As musician and producer, I am beside anything related to protecting IP, however, when I can't even access my own IP, there's something wrong... (So I am besides anyone who purchased music legally and faces the same issue !... )
So, just in case someone has an explanation or suggestion (update) to this frustrating issue, I am asking this question again...
Thanks,
Rob

A month and no one has a clue ?? ....
I'm not alone on this one, c'mon guys !

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