Discontinued vs Continued by manufacture

I have an ipod 4th gen 8gb and it has been in a critical condition ever since last year (November 2014) and I think fixing it now is a bit of a waste of money due to the new product updates. I have many great songs in my ipod that I would not want to lose; I attempted many times on trying to transfer my music into another device but that didn't work, or maybe I don't know how to transfer, could you help tell me if transfer is even possible and if so how?... also, I have been looking up online deals for ipod 5th gen 16~32gb ($199~250) or an iphone 6/6plus 16~32gb ($703~815).. which one do you think that is more reasonable in circumstances? Another one is I need a new computer so I have been thinking of purchasing Apple products more than other products due to amazing graphic quality and technology; Mac Book pro or an iMac PC, please help