Will your future system be PC, linux, or Apple based? That would determine the appropriate format for ripping your CDs. I'm of similar age and just ripped my collection via my iMac using ALAC format via iTunes (as per JohnR's tutorial posted under the Apple Circle entitled "Getting Started"). ALAC is the Apple equivalent to FLAC and allows for album art to be displayed within iTunes.
Seems that you've got things a bit backwards, should have done some research ahead of you to sort out formats first, then looking for a compatible software and DAC.
Check out the Hi-Rez Music circle for advice on good quality recordings.