I just wanted to add - what seems complicated is indeed simple to start with, but then, over the years, you tweak things, and that's what makes it appear complicated. Here's what I did:
Starting from an analog system with just an old-fashioned cd player added: (I already had a nas, but was not using it for music)
step 1: I added a squeezebox touch. - audio out from its internal dac to my pre-amp. Nothing else, and this was an eye-opener - Now I could play my CDs (once copied to the nas, running LMS) controlled by the touch screen on the squeezebox. The convenience was great, and I convinced myself it sounded better than the CD player. And now had access to internet streaming/internet radio.
step 2: installed a squeezebox app on to my phone and tablet - now I didn't even have to get up to change the music.
step 3: added an external dac between squeezebox and pre-amp. (a beresford dac) - sound greatly improved
step 4: replaced squeezebox touch by raspberry pi/hifiberry digi+ - improved sound, and now on supported hardware (logitech by this time had dropped squeezebox support, but squeezebox software is open source, so no worries there)
step 5.... more tweaks
If I were starting from zero, I might do it differently (maybe an rpi+dac+attached usb disk running picoreplayer with LMS - single box straight into pre-amp). But my point is: Each step was simple. It only sounds complicated if you dont know how and why the system got to be they way it is today.
khozmo passive pre/nytech ca252/cxa252 amps, arc 101 speakers
vinyl: --- lp12/kore/lingo4/ekos2/dv 10x5/gs accession
digital: --- caiman SEG/allo digione, synology nas, rotel 965 cd