Can't play some uploaded content on other devices/mac's.

I have an issue where iTunes refuses to play some uploaded content on my iPhone, iPad and other Mac's in iTunes. It's not purchased content, it's originally ripped. Even if it were purchased my authorized devices are under five total and I'm on authorized systems. Any thoughts? Is there a way to attempt to re-upload the affected tracks? Any root cause or way I can determine which to work on without stumbling across them during playback?
I'm up to date on all iOS versions, the Mac and Macbook are on OS X Lion with all software including iTunes up to date. Any thoughts are appreciated. This is annoying me and turning me off of Match.
Thanks!
Derek

On the source iTunes Library enable the iCloud Download and iCloud Status fields in the Song view. Sort on iCloud Status - by carefully scrolling through you can assess any patterns for the known missing Songs, this should allow you to identify any others 'yet to be discovered'.
First make a secure backup of all of your Song files.
Copy the 'problem' Songs into a playlist.
Burn the playlist to audio CD.
Delete the Songs from the Library & iCloud.
Set the import from CD settings to 256k ACC.
Sign out of the iTunes Store.
Import the Songs from audio CD into the library.
Sign in to the iTunes Store.
Start iTunes Match and allow the 3-step process to complete.
Confirm status of the Songs in the Song view, sorted on iCloud Status - provided they are matched or uploaded - for each computer sign-out of iTunes Store, restart, sign-in to iTunes Store and start iTunes Match - for each IOS device turn-off iTunes Match, select settings, general, music and swipe to delete all, restart the device, enable iTunes Match.
Do let us know the result.

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