Just curious, are you planning for streaming, local file playback or cd with transport? My system is not in the same tax bracket as yours, but I found a good similarity in sound with a tube buffered r2r NOS dac playing local FLAC files off my network (server pc -> streamer Pi -> DAC). That should hopefully mimic the natural analog sound you're used to (and basing your opinions from). Combine that style of DAC with a good streamer, spend good $ on usb or spdif rca cable (highly recommend Hapa Audio Aero cable for this) and leave a few $ for an ethernet cable. @ghdprentice is right with his analysis that a good digital system is almost $/$ the same as a good analog one once you get above the entry to mid-fi market. I've been slowly upgrading each side and finally have them close in performance (analog slightly better still) so I know the struggle of adopting both sides into the same system.
Hope my rambling helps,
-Lloyd