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

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.

Another boomer here who also recently got into audio streaming. I went with the Cambridge Audio CXN-V2 network streamer for the simple reason that most of the reviewers stated that it was an excellent first unit with surprisingly good sound. I will vouch for both. It has an internal DAC with analog outputs, and also digital outs for use with an external DAC. I have been using the internal DAC and have no complaints with the sound. It was easy to set up, and Cambridge's StreamMagic operating system makes using the available streaming services very easy. I have been using it on a trial with Qobuz and have been very happy with it's performance, along with Qobuz's selection and Hi Res offerings. It has a nice full color display that shows the album cover and other pertinent information about the track playing, and putting the StreamMagic app on your smart phone gives you full control as well. It also comes with a full featured remote, but I prefer to use my smart phone. A pleasant surprise is that the CXN-V2 also recognizes my Sony HAP-Z1ES server as a music source since it is on the same network. I run both units on an ethernet connection rather than WiFi.