Joe, until recently, I was in exactly the same spot as you. Not that I dropped out of music (mostly classical music for me), but I was strictly a CD and SACD man. About three years ago I decided to explore the world of digital downloads. For that I needed a DAC. I got one (Emotiva XDA-2 Gen 2). I
downloaded the files to a computer that I considered surplus from other duties. It needs to be pointed out that your PC or MacBook already has a built-in DAC. I'm not sure if there's a way to feed the output of your computer's DAC directly to your pre-amp. But if I was going to be playing hi-rez files -- i.e., beyond redbook CD specifications -- then I needed a DAC. Allegedly a good DAC will yield better sound than any computer's built-in DAC, but I've never made the comparison. So I was playing a few hi-rez downloads stored on the computer's hard drive and fed to the DAC, and everything else was standard CDs and SACDs, played the old-fashioned way through my Oppo BDP-83se universal player.
That's were things stood until I attended an audio show in L.A. I was impressed that every demo that didn't use a turntable had the manufacturer's rep cueing up music on a tablet or laptop. In fact, I didn't see a CD player anywhere in the entire show. In every case, the music was stored on a hard disk drive somewhere and then played through a digital player, of which I saw several brands. I wanted to be able to play my music as they did at the audio show. So very early this year I bought a Bryston BDP-pi digital music player, and I began "ripping" my CD collection to a Western Digital Passport hard-disk drive for play through the Bryston. I originally intended to rip only a few favorite items, but ripping CDs to the Passport became a regular spare-time activity, done while watching TV. A good chunk of my collection is now on the Passport drive. Now, I know bits are bits. But it seems a lot can happen downstream from the disc. It is my considered opinion that the bits played through the Bryston BDP-pi and Emotiva DAC sound better than they do through my Oppo.
The next frontier for me is streaming. It appears to me that the USA is not currently a good environment for classical music streaming. The big streaming sites are (I've been told) set up mainly for pop/rock, and locating specific classical selections can be frustratingly difficult. That may change if we ever get Qobuz or Idagio (European acquaintances rave about Idagio), but classical-music streaming is still mostly in the future in the USA.