I went through the same thing a while back. Thinking about it, it was a good 10 years ago or so, so I guess time flies

IMO we really need to put the sound quality stuff aside for a bit and ask what the advantages are in going discless. I looked into it because I got tired of getting up and changing discs. While my discs were all neatly organized, I got tired of looking through them for a particular song or two. Looking at all of them, I got sidetracked in that I started seeing stuff I hadn’t listened to in a while and wanted to listen to that instead, then seeing something else, etc. I was quite ADD about it. But mostly, I found myself seemingly getting up and getting discs more than I was sitting and enjoying the music itself. I figured making compilation discs would help, like the old-school mixed tapes I used to make, but it didn’t.
Then my CD collection started taking over the room. I’m a minimalist by nature and an OCD guy in the sense of not wanting to see anything out of place. I found myself reorganizing my CDs constantly - alphabetically, by genre, by era, all that stuff. Then I’d get a new shipment of CDs and the whole collection had to be moved and reconfigured. Yeah, I’m crazy. Don’t judge

But my main thing was I traveled quite a bit for work, and got used to my iPod. I could actually sit and listen without fussing about with physical media. I thought it would be a perfect world if I had the iPod convenience with my system at home.
I bought the Apple TV generation 1 with the built in hard drive and optical output. I also bought a several generations old Theta DAC my local shop had laying around for about $150 to see if the whole thing had any potential. I haven’t looked back since. I don’t miss the physical media at all. I still have my turntable and LPs, and that easily fits the bill of handling media and that whole ritual.
I keep it as simple as possible. I run iTunes on my laptop, throwaway USB cable to my Rega DAC, and fed to my Bryston B60. Done. And it sounds fantastic. It could sound better, but couldn’t it ALWAYS sound a little bit better? Actually, I control my iTunes with my iPhone, so it’s not like I’m sitting with my laptop on my lap. And I have all of my music stored on an external hard dive connected to the laptop.
I sit down and listen to music. I’m not fiddling with WiFi issues, server issues, software issues, gear and computer program of the month issues, subscription issues, streaming service being down issues, playlists not showing up issues, etc. I just sit down and listen to music. Whatever I want hear that I own. Just like when I was in an airplane or on a bus. It works when I’m sitting and listening actively, or as background music when I’m doing stuff around the house. Or when there’s a bunch of people over. I can be on the other end of the house and change what’s being played. I can set up a specific playlist or play everything on random. And I can go over to the laptop and switch over to SiriusXM. That’s not really possible with a CD player. Or at least a single disc CDP.
All of that is keeping the system is simple as possible. Hard drive-> laptop -> DAC -> amplification. When I move into a bigger house, I’ll get into stuff like Bluesound with speakers in different rooms and all that fun stuff.
If none of that convenience means anything to you, stick with the CD player. If you think it’s enticing, try it out. I’m sure you’ve got a computer and hard drive. Get a cheap DAC and connect it to see if you’d rather move that way. If it works out, upgrade to your heart and budget’s content. If it’s not worth the effort of going forward, move on.
With the quality of DACs out there, sound quality isn’t the determining factor anymore IMO. It’s how you want to interact with your equipment.