Fully Digital Playback?

I am looking for some input on the easiest and most efficient way to fully digital music. I am putting together a system from scratch as I sold my whole system when we moved into a condo. My last CD player was CEC TL51XR that I was very happy with due to its analog sound. I am confused about how many pieces are needed-streamer, transport music files etc.. I am just not knowledgeable about any of this. I do have quite a few CD's so I was thinking a starting point would be a modern cd player with a very good dac and usb? I would be looking to keep the whole shebang under $2,500 if possible. Also, do music files still sound crappy? Thanks