Ipod classic music to Mac Book Air

I am a new owner of a Mac always used PC in the past, and have an Ipod classic from a ba-billion years ago (2006)
My old PC computer died.
My old itunes account was attached to an email that got hacked and I can no longer use.
When I try to log in to the account through apple it says my birthday is wrong. (I know when I was born) so I assume this has to do with my email being hacked.
I cannot get purchaced music off my ipod.
I also keep getting an error message everytime I try  to transfer music from the "harddrive" option of the ipod classic to the new computer. I have music going back as far as 2002 on this ipod from several different computers, cds, etc. All paid for! Nothing stolen, but I cannot get it from my ipod to my new mac Its so frustrating because I didn't hack anything or steal anything and now it looks like I'm either going to never buy new music for my ipod or erase and start all over...
Any advice to keep all the music would be appreciated!
I never had any problems transfering from one computer to the other with a PC does apple do this on purpose? It really makes me wonder if I made the right choice if everything is going to be more difficult on my new Mac?

Also I cannot get the ipod to stay connected to my Mac for more than a min??
Everything about this switch is annoying and doesn't make sense. It's an apple product trying to work with another apple product so why is it so much trouble?

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