160gb iPod classic music transfer to PC helppppp

I have had an iPod Classic 160gb since 2008. I spent endless hours transferring almost 600 CD's to it. I did it once and never got all 700 and some CD's transferred. Most of the music is Apple lossless. The PC i used to run iTunes on initially is long gone. I am a PC geek for building and go through PC's about every 6 months.

So... I do not want to go through this again and rip cd's to my latest PC. I did have all the music stored on a hard drive once but again, have lost that too.

Is there a way to take the iPod's music file and convert it so my iTunes will recognize it. I really do not want to go through this whole thing again but if I have to, I guess I will have to. I recently put a new battery in my iPod (larger and more capacity which will not allow me to close the case all the way, but I can live with that).

I did at one time transfer all the music from the iPod to a PC and found a program that de-scrambled the file structure. But again, I have no idea what ever happened to that hard drive.

Lastly, what would be the coolest if is i could getting iTunes to recognize the amount of time I put into the iPod and just say hey, lets just sync iTunes.... WITH MY IPOD.

I of course understand the whole copy write thing but if you want to see a pic of my CD collection, I would be happy to provide that.

Thank You for your help.

garrett P.