Let me preface by saying I know nothing about networking, software, or computers and technology in general besides the most basic utilitarian knowledge needed to get by daily. Back in the HiFi Guides days, I also documented my growth in the hobby. My Nobsound tiny little hybrid amp, my Darkvoice, and my Sivga 6’s, CAL-1’s, Monoprice retro’s and other very basic equipment went on a journey of growth.
I was unfortunate in that my first good piece of kit was an EXOGAL Comet+ DAC which when paired w/ a proper more updated front end scaled in performance and it was very easy to understand and hear the difference even early on when my ears and equipment were still in the beginner growth state. 
I absolutely found it ABHORRENT and hated myself for being able to actually hear and justify the difference in the quality of sound character that a good USB cable made, and I’m not talking about $100 or $200 my dealer made sure I understood that quality cost blood
money

Again, early on I made the choice to rent my music via streaming services and rather than nit-pik and hem&haw over the cost I went all in on Quoboz and Tidal and finally ROON to tie it all together. I tried do go cheap for a while, I tried to go w/ CD’s, mp3 files taken off you tube, hell I even tried to collect music from folks…All wasted effort, rental streaming works best for me and it has simply become a $50 monthly expense. Add my $80 monthly internet bill and we are talking about $130 monthly, and then $1560 yearly. This is ALLOT for my musical enjoyment…
@Veritas probably remembers those early years better than me, some of the late evening conversations, forum posts etc. what I DO REMEMBER though is that it just clicked one day in my mind. “Garbage in, equals garbage out!” Just like folks who use Vinyl records look for albums that had a great recording studio set, and pressings that were of good quality then they move onto the cartridge quality, tone-arms, plinths, isolation and so forth. The trick is though that once you have your room, seating position, amplifiers and speakers ready to go, you need to FIND good music that matches the effort you put into the back end and that requires you go all the way to the source. 
If you are still following along, the source, in the case of streaming starts in the recording studio, then moves along the digital path from there. Thus somehow since the interior makeup of a single capacitor and strands of wire can make a difference in sound character and presentation, in my simple-minded view then the quality of the signal coming into the house makes a difference too. Thus I upgraded the stuff which technically makes no difference to the sound quality or character as stated by half the folks who are masters in the fields of technology. The other half want to sell me all sorts of fancy stuff 
Most of this is wasted breath, my most used system in the house, in my kitchen, is played via YouTube and free Spotify, the speakers, amp and cables all total less than $500 invested new. Plays great, images pretty darned good considering the location of the speakers and actually sounds good 
Does my living room system sound better? Yes it does.
$50K + better?
It no longer matters. Once you’re into a hobby deeply, any hobby, only your own experiences, desires, beliefs, and monetary constraints matter any more.
Happy listening to all 