Sync & auto convert high-bitrate songs - many songs skipped
I have a large library of Apple Lossless music that I've ripped from my CD collection, in iTunes 12.1 on Windows 8. When syncing to my iPhone 6 with "Convert higher bitrate songs to AAC 256k" selected, anywhere from 10-40% of the songs being added appear on the iPhone music library, but will not play. They just get skipped over and the next song starts.
I've watched the syncing/converting process in iTunes closely, and I can see this happening in real time: with my iPhone music library visible in iTunes during the sync, I can see each track being transcoded in turn, with a little progress circle that gradually fills up as the track is transcoded.
For most tracks, this takes 5-10 seconds, but for some, it appears to happen instantly - it seems that iTunes is not actually transcoding them, but it thinks it has, and the song is indexed in the iPhone music library even though it has not been properly transcoded & synced.
I've tried unchecking an album, syncing again to remove it from the iPhone, then checking it and syncing again to add it back. Same thing happens, though with different tracks missing - it seems random which tracks transcode & sync properly and which end up missing.
The result of this is that I have a 128GB iPhone with a music library full of partial albums, each album missing a few (or many) tracks. This is incredibly frustrating, to say the least.
Has anyone else run into this problem and come up with a solution?
If not, I may have to just sync the full ALAC files to my phone and sacrifice storage space. Wouldn't it be nice if this useful feature actually worked?
iPhone 6, iOS 8.1.3