What I always find interesting is people who spend a lot of money on their analog system; turntable, arm, cartridge and phono stage and then spend a bare minimum on setting up a digital system and talk about how analogue sounds so much better than digital. I am not saying you will fall into this trap just that if your analogue system is a lot better than your digital system this is how you will feel.
If you want digital to sound as good as your analogue set up then spend close to that amount and don't limit it to a third of your analogue's cost. Go for the Rose 150 or something in the $5k area. Just your turntable and cartridge falls into this range. Once you begin to enjoy the convenience of digital you will stream equally to playing vinyl and maybe more I am guessing. This is not because you will like the sound better but the convenience is there in terms of ease and access to so much music. Why end up feeling like you want to upgrade so soon from starting your streaming adventure. If you have the money available buy something in the $5k area. You might just want to go to some highend audio stores where you can audition and compare a $5k system to one half the price. If you don't hear a difference then you saved a bunch. Also compare the two price points not just to themselves but to an analogue system equal to yours at home.
If you do own CDs then I would suggest ripping them to FLAC format and stream your digital files and explore ROON which will manage your digital files and integrate with some of the audiophile level streaming services like Qobuz and Tidal. One of the nicest things about ROON is their ROON Radio that will integrate with one of the streaming services you subscribe to. This way you will explore a lot of new music that falls into the type of musical areas you enjoy.
Your iPad will be your control center, nothing I have found is easier but I do have a very large digital library.