Question/Help Needed: Boomer who is totally inexperienced with DACs and streamers.

As a boomer who wanted to do the same thing as you a few years back. I went with a Bluesound. It was easy to set-up and understand, the software is solid, their help desk is great, and the quality was well worth the price. This all helped me to get me started and to finally understand DAC's and Streaming. I kept it for two years or so, until I got upgrade fever. I was then able to sell/trade the bluesound easily for a good price also. 

Just my boomer experience, there are many good products out there, many are better/more complicated then Bluesound, as others have started, but Bluesound made it easy to get started and does it all in one box. 

Hope this helps.

Brother Boomer here...

I started my streamer journey during the Covid shutdown with the Wiim Pro. I find it very easy to use with Amazon, Tidal, or Spotify. Good sound quality as well. Under $150 it is a steal. Have fun.

Fellow boomer here as well.  The advice of @arize84 is, in my experience, sound.  When I needed to move into the streaming world, I went back to the dealer who had sold me my kit in the late 1990's, and he hooked me up.  I am currently using a Linn Akurate System Hub to stream on my main system, and a Blue Sound Node 2i to stream on my secondary system.  I use Roon on a Roon Nucleus media server to run both systems from my iPad and from my iPhone.  I use the Qobuz subscription service to source my music.  I am very happy with all of the above kit and services, which my dealer tailored to my particular needs, budget, existing kit, and tastes.

I hope your experience of streaming turns out to be as pleasant as mine has been.

WiiM Pro Plus.  Very good reviews and inexpensive. 

There are many options as you can see.
IMO, for someone just starting out Bluesound Node is your best bet. They’re easy to use, have been around for a while and support a wide variety of streaming services, including Amazon. Use USB to connect to your dac and you’re good to go.