Music files don't transfer to iPad

I desperately need help!
I've upgraded my iPad from the first retina version (running iOS 6) to the last retina before iPad Air. The "new" iPad is running iOS 8.1.2.
I'm running iTunes 11.4 on an iMac 27" running OSX 10.9.5.
After the switch/upgrade I cannot get my music library to synch with the iPad. Since I have about 60gigs of music in iTunes I've created a (smart) playlist with the music I want to have on my iPad.
If I goto "On this iPad" in iTunes, and chose "Music" I can see the songs I want to synch, but they are greyed out with a circle before the song name. Now, this is, I guess, what music in the cloud would look like but I don't use, and never have used, Music Match.
I've searched forums for solutions and have tried the following:
- Restoring the iPad from the last backup. Doesn't help.
- Deleting my iCloud account from the iPad, making a backup of the iPad, restoring it from the last saved backup without an iCloud account. Doesn't help.
- "Unsynch" the music from the iPad (that really isn't synched anyway). Making a backup of the ipad. Restoring it. Set the iPad to synch the playlist. Doesn't work. I end up with greyed out music.
- Restoring the iPad from the last backup of my old iPad (that ran iOS 6). Doesn't help.
During all these attempts the only music files I've ever got to transfer to my iPad have been music purchased in iTunes (and since I'm old fashioned and prefer to own music in physical formats that isn't much).
The only thing I haven't tried is to restore my iPad as a new one. I haven't done this since I will lose quite a bit of data and I refuse to accept that Apple have created new software that prevents me from doing what Ive always done when purchasing a new iPhone or iPad; pluggin it into the computer and restore from the last backup of my old device and then continue using it as before, without any hassle. Since I've, until now, refused to upgrade my devices to iOS 7/8 I'm pretty sure my problem is caused by iOS 8. I'm also in the process of upgrading from an iPhone 5 (running iOS 6) to an iPhone 5S (running iOS 8) but since I'm having this problem with my iPad I'm pretty sure I will end up in the same problem on the iPhone. So at the moment I'm stuck!
Is there anything else I need to try?

OK, so I have now tried migrating from iPhone 5 (iOS6) to iPhone 5S with the latest iOS8. And as I expected I'm having the exact same problems with my music files that won't transfer to my iPhone, just as they won't transfer to my iPad.
Any suggestions?

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