My friend, if you think I am “barking up the wrong tree”, then I know you are “lost in the woods”, and I’ll tell you why. It’s that you “did not get” what I was saying, so pay close attention. I am only going over this one more time to help you out so you can listen to your iTunes music; even if you have an old iOS or device getting in your way and preventing you from doing so.
Do you know what the iTunes Media folder is and what it is for? Maybe not, so I will tell you. It is the folder where the iTunes program stores all you music, videos, etc, that are cataloged in your iTunes database. It is full of music albums by artist with music tracks inside that you do not need the iTunes program for or even running, to listen to. On a PC, you can click on any file in folder to play q track; likely so on a Mac, too, but I don’t have a computer called Mac to find out for sure.
As an extreme example, meaning using an old iPad 1 with iOS 5 on it, I can play any of the music in my iTunes Media folder (including music I added a moment ago). All I need is a music access/playing app on iPad that can access the My Cloud on my network and play from the folder, because I have a COPY of my iTunes Media folder stored on the My Cloud. Some people even direct the iTunes program to save the iTunes Media folder on their My Cloud instead of in the iTunes folder of their computer. You could, too.
Although this ensures an up to date media folder to listen to, I consider it too risky since it is the one and only “original” copy of iTunes Media that gets touched by iTunes program, and I do not want it damaged in any way, so I always make a copy of folder and put the copy wherever I want; like on My Cloud, a wireless drive or any other places I want access to it. I could even give it to someone to put on their PC or My Cloud, and they could play my music collection – even if they do not have the iTunes program, because it is just music files inside the folder!
The only drawback is I need to keep my folder copies up to date, and I do.
So, quit your griping about iOS versions and WD and copy your iTunes Media folder to your My Cloud and start enjoying your music on any device that can access your My Cloud.