My macbook wont sync the music i downloaded onto a flash drive and onto the mac book what do i do?

My macbook wont sync the music i downloaded onto a flash drive and onto the mac book what do i do?

If you subscribed to iTunes match the songs are kept in icloud. If you didn't but you did save the actual iTunes library folder which should include the music, video, etc.  you should be able to just drag this file back to your machine in the same place and when you open iTunes it will give you a chance to identify the iTunes library folder. 
You can test this to find out if you saved the media files or not and don't need to attach your nano to do it. 
You are correct that once you connect the nano it will clear the existing files from it and sync it with the new iTunes library. 
If you don't have the media files i'm not sure if/how to get them back on a windows ipod.  I have everything backed up regularly because of the horror stories I have seen & heard.

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