Download music but only one songs seems to transfer

Can somebody please please help me! I have tried on numerous occassions to make this device work with me, but it aint. I have erased all songs and freshly added more to the shuffle, only to find that one song has actually been added. This cause a problem as on many occassions I have sat there for hours adding songs and albums only to find that I can listen to one out of um let's say about 100. If somebody has a easy solution I would love to hear from you. Thanks

Stacey - Let's start troubleshooting here, Go to iTunes, select one of the songs that you'd like to transfer to the shuffle that never made it and click on it. Then click CTRL + I. A window will pop up with information on the selected song. Can you tell us what it says next to each of the following entries?
1)Kind
2)Size
3)Bitrare

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