Music from iPod not showing up on new computer

I recently purchased a MacBook after using iTunes with an HP laptop. Once I hooked my iPod up to my new Mac, many songs that I downloaded from sources other than iTunes and from CDs I had burned onto my iPod did not show up in my new iTunes.
Also, any new music I purchase from iTunes, if I want to put them onto my iPod, iTunes tells me that I must erase all other files before adding my new purchases.
Ideally I would like to keep all of the existing music from my old iPod and have it transfered to my new iTunes library.
What do I do?!

Start here:
iPhone, iPad, or iPod touch: Device not recognized in iTunes for Windows

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