It would be great to see your system / venue. There is a place under your UserID to put it. Really helpful for us to be able to help.
You can see my systems. In mine, my really great analog end sounds the same as my digital end. I am happy with both. I worked on my digital leg… well since the release of the CD.
Lessons: pursue your DAC and streamer the same way you would pursue any other components. Separates, not combined units. In general, the cost of your (carefully chosen) streamer = DAC = preamp = amp = phono stage. All, require top quality, carefully chosen components. I recommend Aurender (or Linn) for streamer… but streamer only. If your budget is $15K then you want to split between the Streamer and DAC. You might get a used high end DAC and a new (best you can afford) Aurender streamer.
Once you have a high end digital system all of those CDs and ripped files become virtually worthless. In my system I cannot tell the difference in sound quality between a CD, ripped CD, and streamed version… but frequently my streaming service (Qobuz… this is the one you want) will have higher resolution versions available and they will sound better (Qobuz has over 1/2 million high resolution albums). So, while I loaded up my ripped CDs… I never use them… why would I? Usually the streamed version sounds better and I am completely lost in new music anyway.
The take away is that, if you do this right your $12.99 / month subscription will give you access to millions of albums and you will no longer have to buy music… so… this gives you reason to take your time and get the best streamer and DAC you can… making stretching worth it as music cost goes down. Sell your CDs while you can. I gave mine away.