OP. I am new to streaming after 50+ yrs of analogue combined with 10 yrs of playing ripped CDs (AIFF) on my Mac Book Pro through my pre. I too was daunted by all the rapidly evolving technology. I finally went to a local dealer, Jonny Rutan at Audio Connection, and he got me started on a nice easy path with which to begin my streaming journey.
I bought an Auralic Altair G1 streamer/DAC one box solution. I am ecstatic. It is so simple and the quality is extremely good for the price of around $3,500 USD. It punches way above its price point. For years I resisted streaming because it seemed so overwhelming, and now I have the world of music at my fingertips. BTW I use Quobuz.
Do yourself a favor and find a dealer to work with if you feel the need to jump right in and build a really high-end system. But if you don't mind going slowly like I am doing, then the Aurelic Altair is a great starting point. Enjoy the journey.
Bruce