Hello APoke33, I had just this journey.
-Started with apple computer airplaying to apple TV to audio
-upgraded to Bluesound Node...nice improvement
-Added Roon Nucleus+ and bought lifetime subscription
At one point, using Roon, I had Node in one system, PowerNode in bedroom, and Pulse 2 mobile speaker. Yes Bluesound is nice and plays well with Roon. Istill use the Pulse 2.
-upgraded to PS Audio Direct Stream DAC w onboard streaming card (bridge)...nice improvement
-upgraded to Auralic Vega 2 Streaming DAC (can get used for under 4k)...big improvement.
-upgraded to Mola Mola Tambaqui Streaming DAC...HUGE improvement
-added Auralic Aries G2.1 Streamer...big improvement
-added Network Acoustics MUON filter system...big improvement
I was able to easily sell all the old DACs here or USA.
Along the way I did most of the upgrades in the digital chain you discussed;
-Nucleus and my Bonn 8 switch on linear power supply (HD plex, two outputs)
-iFi Power Bar with iFi power cables and iFi power supply for the Modem.
-All the short cables are Supra Cat 8
You need a resolving system to hear all these upgrades. Did one particular small thing make a difference? Hard to say. The major upgrades were obvious, but I do feel everything matters.