Started 15 years ago with FLACs and JRiver MC (or whatever it was call way back then), first with a SoundBlaster card (and a spdif daughter board).
This was then upgraded to an M-Audio Delta 410. Various adventures with AV automation and multichannel audio (DVD-A, and esoteric formats) ensued
More recently, I've seriously rekindled my interest in digital audio, starting with an SB-Duet, soon adding a Touch, and now using 2 SBTs (both with EDO) and 2 SB Radios around the house.
Servers have ranged from Netgear stuff, to a silent solution (Vortexbox in an HD-Plex chassis) and currently an HP Microserver D54L with WHS2011, keeping the vortexbox as a backup
My DAC adventures have been straightforward by comparison: Theta DSPro-IIIa followed by MDAC (subsequently upgraded to Fusion-L3), using a Behringer UCA202 to play while the MDAC was being upgraded.
The rest of my stereo system hasn't evolved much by comparison (same ARC tube amp and Mani-2 speakers for 18 years, same Revox tuner and Dual CS5000 record player for 25 years)