Why do I need to re-download my songs from iCloud if they're already in my cloud?

Why do I need to re-download my songs from iCloud if they're already in my cloud?
I have iCloud on my iPhone 4S with iOs7 and I have both added all my Music on my iTunes to my phone manually and also have them on my cloud. Under iCloud settings on my phone I have "Show All Music" toggled "On". When I'm driving and want to listen to a certain song, most of the time the song I want is grayed out, unable to be played by my phone, and the only option I have is to "Re-download" it from my iCloud--I get this little picture of a gray cloud with a red downward arrow displayed and my Music takes forever to load. I also get this annoying pop up message telling my I might be subject to additional data fees for .....re downloading music I've already downloaded. Its' annoying.

Welcome to the Apple Community.
Content needs to be on your phone before it can be played, if it isn't you need to download it. If you see content with a cloud icon next to it, it's telling you it isn't on your phone.

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If your country's iTunes Store allows you to redownload purchased tracks, I'd delete your current copies of the dodgy tracks and try redownloading fresh copies. For instructions, see the following document:
Downloading past purchases from the App Store, iBookstore, and iTunes Store
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The problem you describe sounds like a bad network speed. Did you say you're uploading stuff to iTunes Match at the same time you attempt a download? Cause that might be the cause.

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Hey goddesses,
Thanks for the question. Yes, iTunes Match requires an active internet connection. However, you can download your content to your local drive for offline use.
iTunes Store: Subscribing to iTunes Match
http://support.apple.com/kb/HT4914
iTunes Store: Troubleshooting iTunes Match
http://support.apple.com/kb/TS4054
iTunes Match: Understanding the iCloud Status icons
http://support.apple.com/kb/TS4124
Thanks,
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Why when I try to re download my music it says this device is already associated with another device and I have so many days to re download my music back? How do I get around this and get my music back?

It is telling you that the device has been associated with another Apple ID. Once an Apple ID has been associated with a device, there is a 90-day waiting period before another Apple ID can be associated with that device. Here is a Support Article that explains the 90-day waiting period:
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Cheers,
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Why do I need to re-download my songs from iCloud if they're already in my cloud?

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