For me the DAC/Server thig is a matter of budgeting to Moors Law. My hypothesis is that Moors Lew applies to digital stereo too and as such products will both double in value and halve in price every 18 months,
For my age/ears/budget I bought a wonderful used PS Audio Perfect Wave DAC and a PS AirLens for my source. I paid for it by selling my beloved Audio Research AP 15 (also depreciating as people figure out preamps are being replaced by DACS and one does not need both.)
I'm a practical HiFi guy so this works for me for now. I'm likely to get the itch to switch next summer :)