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

You really should go spend time with a good dealer. 

your best bet is to upgrade your nad to a naim uniti star this is a far better amplifier then your nad and it has a fantastic dac and streamer built in

Dave and Troy

audio intellect NJ

streaming experts

Check out Roon app and Nucleus+ streamer

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.