My Book Live - backing up an iPod classic

I’d appreciate any help with this.

I have an iPod classic with approx 11,000 songs on it.

Earlier this year I bought an Mac book pro and a My Book, with the intention of transfering my music from my Ipod to the My book live.

I’ve tried this several times but I get to around 5,000 songs transfered - using a program I was recommended called iRip and the process stops.

I live in constant fear of losing my songs!

Any help appreciated.

I would first transfer the songs to the PC, once those are completed, at least I would know I have the music on the IPOD and the PC. Then those can be backup.