I would also try to transfer iPod music with an iTunes alternative.
iTunes alternative to manage or transfer iPhone iPod iPad music
You just need to import your songs into iTunes library, then make a playlist with the songs, connect your iPod to computer, iTunes will detect the iPod automatically, then click iTunes menu "File -> Sync iPod", the songs will be transferred from iTunes to iPod.
If iTunes not works for you, You may try this ipod transfer, it's a nice iTunes alternative that can help you manage iPod files including delete, upload, play, copy, etc. It's much easier to use than iTunes.
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