I can't transfer some songs to my ipod from itunes

I subscribe to itunes match. When highlighting certain songs in itunes where a cloud symbol has appeared next to them, I get the following message: "the song................could not be used because the original file could not be found. Would you like to locate it?" If I press the locate button it takes me to a windows file search screen (giving me no clues as what to do next), but if I cancel it finds the song and an arrow appears at the base of the cloud symbol next to it. If I click the symbol now it eventually disappears and the problem seems resolved. ie it plays when highlighted and can be dragged and dropped onto my ipod. On other songs the cloud symbol appears next to them but with an exclamation mark in it and "Error" in the icloud status column (Whereas "matched" appears next to the others). I get the same message as before and if I cancel the song is found. The difference is that when I now click on the cloud symbol, I get the message "The item was not added to the iCloud as an error occurred", the exclamation mark reappears, "error" remains in the icloud status column and the song will not drag onto my ipod. I can't find a way round this.
I manually manage my music and am preparing to revert to syncing my ipod . I have many playlists in itunes and looking through them there is a scattering of these cloud symbols throughout against random songs. The clear symbols I can alter as above (though it will take ages) but I don't think I will be able to sync the ones with the - ! - mark in the cloud symbol next to them. I have in excess of 10,000 songs - 99.9% from my cd collection.
This is very frustrating especially as these songs I have manually stored on my computer from my cds but iTunes match appears to be denying me access to a significant amount of them. Any help would be appreciated.

See this older post from another forum member Zevoneer covering the different methods and software available to assist you with the task of copying content from your iPod back to your PC and into iTunes.
https://discussions.apple.com/thread/2452022?start=0&tstart=0
B-rock

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