Ipod replacement recomendations please

[indyglyder]

I currently have an Ipod and use the Ipod direct control with my Ram 1500 stock stereo.  I want to replace the ipod with a better portable digital music player. the most important factor is it must be able to be controlled from my head unit like the Ipod via usb.  

other huge pluses would be playing files like Flac and WAV, and possibly having the ability to play music bypassing the DAC directly to my head unit and letting the head units DAC do the work. 

thanks in advance.

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[nauc 10+ year member]

which iPod do you have?  Nano? Touch? etc

 

[indyglyder]

Its a Ipod classic upgraded to 256 SSD.  Its mostly filled with lossless music.