"This one still needs plenty of work. I am currently using a 3rd generation IPOD spooling uncompressed WAV files. I have been thinking about going analogue but have no idea where to start so any help would be greatly appreciated"
Try using Apple Lossless. it's bit for bit as the orignial. It saves space, most cd's are fitted to 350 MB using Apple Lossless. No Sonic degridation.
I personally have the the Apple Airport Express.
read this Apple Airport express Sterophile Follow up
and I have plans connecting it to a external DAC then to the the Sonic T-amp drivin' Fostex FE103E in 5L BR.