Well, also considering I have been on Apple for two days reading through everything to try anything possible from manually trying to get the songs off my iPod to downloading a link they had up for iPod2PC. Then also tried restarting the iPod, reconfiguring it, scanning it to see if it needs any repairs or to see if my iPod was corrupted, and I tried to go through iTunes where it says download Purchased Songs, and not all of my songs show up. I believe only 30 out of 440+ songs showed, and I've definatly purchased ALL of my songs so they should ALL be there. I've done all possible options listed and nothing is working. And I can't call Tech Support, I live in Germany with my husband due to him being military.
I've tried doing the transfer purchases from iTunes and it only lists a few songs when I know I bought EVERY single one.
Did you use the same Apple ID for all of those purchases?
I got a free gift card 10 years ago (before i had an iPod), created an ID and downloaded the only song I would download for several years. After that computer died (years later), I got a new one and an iPod, but couldn't sync the store purchase to the iPod (the store song did play on my computer, but not on the iPod the way all of my songs from my own CDs would). Fast forward to a few years later when I wanted to buy some songs from the iTunes store, and I had to create an Apple ID, but without remembering that I had one already.
What worked for me was to sign in with my first ID to authorize that one song from 10 years ago, and use my newer ID for the rest of the songs I bought years later. If any of your songs were downloaded with a different ID, that would explain why you only get 30 out of 400+, but that's just a guess on my part. Maybe your husband or any other members of your family has an ID that was used.