Syncing purchased music with iPone and Macbook Pro

Already asked this question in another forum, with no responses.  Ok, I have been having problems for a while with syncing music on my iPhone 5 and my Macbook Pro.  It all started when I turned on iTunes Match about 2 years ago.  I quickly realized it wasn't something I wanted or needed.  I spend a lot of time traveling in rural areas with not the best cell service so it wasn't going to work for me.  I am one of those people who doesn't want to spend a lot of time thinking about my technology, I just want to put the music on my phone that I want.
Anyway, I downloaded an album through the iTunes Store on my phone which worked fine.  A while later my 32GB phone was running out of memory so I just cleared all of the music off of it and started from scratch.  For some reason that ONE ALBUM will not go on my phone.  If I go into the settings on my iPhone and into the Music and turn on "Show All Music" I can see it on my phone but it won't let me download it because it says my iTunes match subscription is expired.  The album appears in my library on my Mac but when I plug my phone into my Mac and attempt to add it, the album doesn't even show up as available to be added.  I tried making a playlist and adding the album to it but the songs don't appear on my phone when I add the playlist through iTunes on my Mac.  I'm running iTunes 11.3.1 (2).  Ever since they overhauled iTunes a while back I've been lost in the sauce.  Any suggestions from the more tech savvy people out there?
Ryan

The underlying issue here is that you have chosen to use POP3 rather than IMAP mail accounts. Only IMAP mailboxes are 'synchronized' by default: it is virtually impossible to synchronize POP3 mailbox content.
For a discussion of POP3, IMAP and mail synchronization options, take a look at the Mail & Address Book - Tiger forum located here.

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