Currently Being ModeratedFeb 4, 2013 12:13 AM (in response to rbirnie)
Try creating a new playlist of the same songs, delete original.
Currently Being ModeratedFeb 4, 2013 6:59 PM (in response to Jimzgoldfinch)
Thanks - tired that, as well.
I finally called Apple Support after much frustration.
Evidently, iTunes Match is quite particular about what it can upload. Since one of my most recently purchased albums from iTunes included a digital booklet, it was also included as part of the album when I made the playlist. iTunes Match will only match items in basic format, no videos, etc. After I removed the Digital booklet (like an extra on a cd album), the playlist then downloaded no problem....sneaky.
Thanks, anyway - perhaps this post will help someone solve the same (yet simple) mystery.