Ipod as library

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hi there, so i have my ipod 80 gb that is formatted for windows and i used my external HDs (which dont read on my mac) on my windows and uploaded all my songs.

are there any programs (preferably free but theres always torrents) that i can use to update songs that i download with my mac onto my windows formatted ipod? my windows ehternet system is all messed up so ill be downloading my music from now on onto my ipod, but if i mac format it ill lose all my stuff on it already..... so is there any program that will just let me put on songs whether its mac or pc?

another problem i have is i would like to have my library as my ipod. for instance, on my windows, i just clicked add folder to library > then added the actual ipod, so all the songs where there, but could only be played if the ipod is put in, and im fine with that.

the former is more important, however the latter would be great too, im sure there are some dual OS friendly ipod liberating softwares out there, arent there?

THANK you in advance for your help!
 
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3.4 Ghz i7 MacBook Pro (2015), iPad Pro (2014), iPhone Xs Max. Apple TV 4K
There is no reason that the Mac should not read the Windows formatted iPod. Pull your music off, plug the iPod back into your PC and click the RESTORE button in iTunes, this will reformat the iPod. Then try it again on your Mac and see what happens. This shouldn't even be an issue unless you manually formatted the iPod to NTFS or some such.

Once you accomplish the first, you can do the second the same way. I will say that using your iPod as an iPod and as an external storage drive for your music is not a good thing. If the iPod has to be reformatted or dies, you just lost all your music.
 
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ok let me rephrase so its easier to understand

are there any programs for mac, that will let me update songs from my mac to my windows formatted ipod? sort of a dual OS friendly ipod software that will let me update?
 
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iTunes WILL do that. The Mac WILL read and work with your Windows formatted iPod. If it is not, you have a problem and need to do a restore on the iPod in iTunes on the PC to make it work. What you already have will work fine, you just need to figure out why it is not. This capability is built into OSX.
 

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