Confused - how to get my Itunes songs to appear on my Iphone 4S

Sooo confused. Some of my songs will appear with the cloud icon and they WILL play on my Iphone 4S. But sometimes a warning will appear: "you may incur additional charges if you download songs via cellular network." I have a Cloud account, but not paying for yearly storage.
If I purchase a song from the ITunes Store via my Iphone, then it appears with no problem in my Itunes on my laptop. But what I have had forever on my laptop does not automatically appear on my Iphone. If it's my music, or I have already paid for it, shouldn't I have it on all devices with no problem?
Today I left my Iphone with wifi on while driving home from work, and the songs that were greyed out earlier with a cloud icon did play. But that's not alwasy the case.
Please reply if you have an answer. It shouldn't be this confusing.

This is a widely reported issue with iOS 7.
Tell Apple about it:
Http://www.apple.com/feedback

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Confused - how to get my Itunes songs to appear on my Iphone 4S

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