Decisions! Decisions! How to get into Streaming and how to get over my Audiophile Roots

After spending days and days googling this subject, I am deeply mired in deep pits of data quicksand trying to decide which way to go to get good sound in streaming my music collection to my good stereo systems.  In other words, I want the streamed music to sound as good as the original CD would if played instead.  (My stereo systems are described here:  https://systems.audiogon.com/users/echolane).

or should I just kick the audiophile to the curb that keeps clamoring inside of me to choose the more expensive route because it’s got to be better.

Here are the choices I’ve  narrowed it down to

A. Should I  buy USB hardrives and hire a ripping company like RipToPlay that specializes in classical music and opera?   And rip to WAV or FLAC or ALAC.   About $500.    If so, I would need to add something like a Sonos Connect in the Living Room which becomes another source to the integrated amp and accepts commands from an iPad app or similar.  $350. Also add Apple TV to TV room stereo which does the same as the Sonos $59.  Easily controlled by Sonos app on my existing iPhone or iPad.  Done.  Total cost not much more than $900.
 B.  Or should I buy a Naim Uniti Core* that rips and stores and serves the music to one of my systems?  $2000.  And Not Done.  
I’d still need to buy a decent DAC that converts its digital signal to analog.   More $$$.   Then, what else would I need to buy  to stream to the TV system and how much more would that cost me??  More $$$.  Total cost could easily exceed $4000.

*Ive looked into Bluesound, Cambridge Audio, McIntosh, Elac, Linn and more

It all seems so simple.  Go with A because it’s much cheaper.
But won’t B potentially give me much better sound?

Here are some of the questions that occur to me:
  
  — Is the DAC inside the Sonos Connect competitive with so-called audiophile DACs?  Would I be really able to hear a difference?  After all it’s just transferring bits.  Everyone it receives is passed on unchanged.
  — Has  the Naim Uniti Core ripper improved enough to add better metadata to my classical music collection than the professional  ripper that specializes in classical?  It seems there are serious deficiencies of the Naim’s classical capabilities, but without trying it, it’s hard to know.
  —The Naim has a reputation for sounding really good.  Why the heck should it sound better than the Sonos?
  — If I choose the Naim because it sounds good and in hopes it’s classical music deficiencies will still allow me to find the music I want to play, what else do I need buy to stream the same music in my TV room system?

As I write this I keep thinking to myself,  What’s the problem?  What’s so hard about this decision?  After all Choice A is orders of magnitude cheaper than B.  But it’s the darn audiophile inside me, the one that  has been programmed to consider things like  this audio cable for $500 sounds way better than this other one for $100.  And this $5000 speaker sounds way better than that cheaper one.   And tubes sound better than digital.  And that more expensive cartridge is way better.....and on and on.