Import music from iPod Classic into iTunes

I have an iPod Classic 120 GB that is still in perfect condition. I got it 5 years ago. I had imported several CD's into iTunes on my family computer and then imported them on to my iPod. I also had purchased some music from the iTunes store, but I had a lot more music that I had imported from CD's. An incident happened where a lot of my music got deleted from my iTunes account. I had over 5000 songs on my iPod from all the CD's, audio books, and purchased music I had imported into iTunes and then on to my iPod. When I plugged my iPod into my computer, iTunes recognized that there was music on my iPod that wasn't in my iTunes library. It asked if I would like to import the music that was on my iPod into my iTunes library. I said yes. Of the 5000+ songs on my iPod, only about 300 were imported back into iTunes, and then my iPod was synced. I lost the rest of my music. After this incident, I took several hours to re-import the CD's back into my iTunes library. Not too long after this, my computer crashed. Everything was wiped from my computer. We started by re-installing the drivers, Google Chrome, and I just re-downloaded iTunes. All the music that was in my iCloud has been backed up and added to my new library. This is only about 31 songs. I'm afraid to plug in my iPod again because it still has all the music on it that took so long to re-import. But now I can't add another CD on to my iPod without the fear of losing everything again. Does anyone know how I can make sure that ALL the music will be re-imported into my iTunes library again when I plug in my iPod? I don't want to go through this ordeal again if I don't have to.

Here is a User Tip from fellow Support Community member turingtest2:
TT2's iOS device to build iTunes library
Cheers,
GB

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