You have some choices when it comes to moving your stack of discs to the cloud. Just about every place you can buy music has some sort of subscription with a free tier solution for ripping, recognizing and lockering your existing music. I use iTunes Match. But I could have gone with Amazon Music, or Google Play; pick whatever makes sense in terms of where you buy most of your music.
I just basically set up an assembly line and had a swim lane for ripping discs. I didn't care too much about how many I did at a time or on a day; just whenever I didn't have something else going, I'd sit down and rip stuff. And eventually, it was all done. Shortly thereafter, I turned the boxes of discs over to my sister to do with whatever she felt like doing.
Because I use iTunes Match, and because I have iOS/Mac everything, I can now listen to my music anywhere. Also, because my kids share my account, I don't have to buy separate music for them. I wish that the Pioneer music system in my car handled multiple bluetooth connections better, but if it is acting up, I can always just plug the phone in and go through the iPod interface instead (altho then the handsfree doesn't work . . .).
I bought nice headphones (I like Sennheiser, so I have a good pair for at home, and I have noise canceling ones for travel, and a neckband style for when I go for a walk alone). It's pretty painless. When I am sick of what I already own, I just go to the iTunes store and buy something. There is a free song every week there, and if you have a Starbucks account, they will message you an iTunes store code for a different free song every week. Should I probably sign up for Spotify, like you almost certainly have? Sure! Maybe someday.
I even bought an Airplay speaker, altho I don't use it very much right now, probably because the kids are at home a lot in the summer. When I do use it, the sound quality makes me very happy.
In the meantime, I can buy a couple Alan Jackson albums when I am in the mood and hit repeat artist and just listen to that until I am sick of it, which is basically the way I've always preferred to listen to music. I am an AOR girl, and that seems unlikely to change, altho the AO part has become more important than the R part over time.