As and old music lover/audiophile ( is there such a thing? ) I will relay my steps towards streaming.
I purchased a really nice dac you may be able to use your CD player. At first I started burning my CDs onto my laptop using JRiver software. For me I really didn't like looking at my computer while listening and trying to enjoy music. I purchased a Melco N1 at 2k. Then a comparable Buffalo burner. Now I burn my CDs to the Melco at the same time I use it to play music. So the Melco is a library and player with 2 terabytes plus unlimited external storage. I loaded up a " remote " app on my IPad and use that to control the Melco, which has its own software.
Now I have almost all my CDs recored and playable. I like the sound quality better then any player I have owned, and I have easier access.
Haven't gotten into streaming yet, a friend of mine had stored a huge collection of CDs, put them on a hard drive which I downloaded to the Melco, now I have so much music don't know how long it will take to listen to all of it. When I get board I may go to streaming.
Just a thought.