Some songs won't download or play from iCloud

So I recently subscribed to iTunes Match to convert about 700 old songs from Protected AAC 128kbps to the DRM free 256. Anyway most of it went over just fine (besides iTunes crashing 20 times while uploading to Match), I converted almost all my old songs to new "Matched" versions, but about 45 songs got stuck and are "grayed out". I can't download or play them. Here is an example:
[IMG]http://i61.photobucket.com/albums/h58/jumpinstocktoyotas/itunesissue.jpg[/IMG]
Rest of the album downloaded fine but that song is stuck. Almost every album that I "matched" has at least one song like this.
Please help! I am getting very tired of all the issues with my apple products. These stuck songs, album artwork disapearing, play counts reseting, albums not grouping together properly, iTunes crashing while uploading to Match, my iPod touch crashing while listening to music... About to drop apple all together.
PC is Windows 8 64bit, iTunes is version 11.0.2.26.
Thank you.

Think I found a clue, I backed up all my DRM protected files before I started incase something like this happened. For some reason the songs that won't match are showing as purchased by my brother, but I know this isn't possible. Look at the link to the pic below, The first track (on top) is showing purchased by my brother, but the entire rest of the album is shwowing purchsed by me. So I'm supposed to believe that he bought one song on the exact same day at the exact same time as I bought the rest of the album? Something is off here...
http://i1251.photobucket.com/albums/hh541/two250/itunesissue2_zps8ef2ead3.jpg
Many albums are doing this, showing one song being bought a different account as the rest of the album, even though time a date purchsed lines up exactly...

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