Music RetrievalFollow

I'll try to make a long story short:

Last spring when I built a new desktop and tried to move my Itunes from my old PC to my new one, it didn't work. And now, there is literally no trace of my music on my old computer, and all the files on the new desktop say something to the effect of "can't find the source file". It was a large amount of music, much of which had been uploaded from CD's which I no longer have. Easily over $1000 in music. No, it wasn't backed up on Icloud. From what I understood at the time, you could only back up music you'd actually purchased from Itunes itself. I've since learned a little more about what I *should* have done prior to trying to move the music, but I'm not really that tech savvy so w/e. Anyhow, I thought I'd lost all that music.

However... I found an old, old Ipod in a drawer that has a decent amount of my music still on there. Is there a way to retrieve the music from the Ipod onto the new desktop? Like I said, I'm not that tech savvy. I've asked around a bit at work and people claim it can be done but noone has stepped forth and suggested an actual process of steps. Any suggestions? I really don't want to be out $1000 in music if I don't have to. This whole situation has made me consider boycotting Apple products because of the level of control they try to exercise over what I can and can't do with music I bought in the first place. Sorry for the rant. Anyone know of a way for me to rescue my music?

Danke!