Apple - How do I put music not eligible for iCloud on my iPhone without turning off iTunes Match?
I made the file kind "audiobook," and then they seemed to sync fine, as audiobooks. Since they were lecture files, that's just fine with me.
Just spoke to Sr. Apple Support staff. There is no official way to do this without turning off iTunes Match, selecting the content you want moved to either the iPhone or the iPad (in iTunes), syncing and then turning iTunes Match back on. While not a great solution, that is the official word.
I changed the file type to 'Audiobook', (Right click on the file in iTunes, Get Info, Options, then change 'media kind' to audiobook') and then it allowed me to drag and drop the file on to my iPhone in iTunes. Then, in the Music app on the iPhone, tap 'More' in the bottom right corner, and 'audiobooks' will appear in the list.
Took about an hour of faffing about with iTunes Match before I discovered this tip. Then it was done in about 20 seconds.