This is where I come back in. Been away.
I used to have a CDX/XPS and adequate naim amplification to go with it. My CD player now is a Wadia 6i, a player roughly contemporary to the CDX, sounds a lot better, though.
I started by using iTunes and an airport express to dip my toe into streaming music. Convenient, but not up to CD direct.
I played with a squeeze box classic, I think it was called, better than airport express, I got lured into macs by the iPod, it didn't synchronize as well as I would like with iTunes. I got hooked by the play counts and the last played date info,etc (part of meta data and tagging). Listening to LP and CD, you don't think about how music is labelled, but it's paramount in computer audio. You music must be sorted, so that you can find it easily when you are in the player software. It's also useful from file organization point of view, too.
I also past through the apple TV, 1st generation with expanded local storage, at least it synchronizes with iTunes, sounded OK, too.
Along the way I acquired a dac, a Chevron Audio Paradox that is non over sampling, I like the naturalness of NOS playback. It has a USB input, I thought I'd never use it. I got the dac after a Lite Dac Ah, which uses the same chips, and for the money sounds really nice.
A few weeks ago I decided to press into service a redundant Netbook, you know, one of those mini laptop thingies superceded by iPads and the like, as a media player, using JRiver as playback software. I still rip using iTunes on another computer to the Nas, a low spec synology. I'll be looking at other riping solutions shortly, but iTunes is a very good organizing tool. I've got so attached to it, that I'm having a hard time not being able, out of the box, to lastname sort on artist name.
So today, it's Nas for storage, NetBook for playback, and rather good Yamaha integrated amp (which I would have snobbed in my naim days). Computer audio has led me to giving up LP playback, I put the TT away last week.