No bro I do not judge people so easily,let alone underestimate, you yourself said "Raspberry and linux to me are bit of a wilderness". Also windows is state of the art for Audio is a pre conceived notion and can be argued for hours (we will not go in to that). My only point was, before even trying you already have decided that Rpi and linux are not good for what they offer in comparison to windows
Like when I was trying to suggest anything related to PCM->DSD conversion I did not post or comment unless I tried out myself, which is what I did ... I never had converted a PCM file to DSD, so could not comment as to how much processor hungry the conversion is UNTILL I myself installed Jriver and had a couple of PCM converted to DSD, I was ready to comment.
You without even trying and comparing have made a preconceived notion that windows is the state of the art in Audio when actually there is nothing you cannot do in Linux that you can do with windows ....as simple as that ...... and that CA (computer audiophile) analogy you give, I can find you quite a few articles on CA itself where people have built an Audio focused machine on linux.
Coming to NUC why on earth is it a dead end,(and that too by design..lol, when in fact they are considered to be pretty decent with the size and power footprints they offer to be able to run any windows based application) ......the mobo you are using "Gigabit B85M-G" (BTW I could not find Gigabit B85M-G,so I am assuming you meant "GA-B85M-D3H", there is an ASUS Board with GA-B85M) anyway uses plain simple Realtek Audio chip, same as NUC, and assuming you will be using USB DAC with ASIO drivers on windows, that is something you can do with NUC as well...