I did start out with a complete CD player but the first separate DAC I bought was a Sony DAS-702ES in 1985 which I used for years, I still have it and it still works.
Next I got a Meridian 606 DAC and matching transport. I also had a Stax DAC-Talent. I PXed these for a Spectral Spectral SDR-2000 but often just used the DAC in my StellaDAT recorder. My final update pre-streaming and multiple file types was a Goldmund Mimesis 20, which I also still have.
Then I retired and had time and minor inclination to compare stuff, and much less spare cash.
I decided to retire the Stella and ended up with Metric Halo ULN2, then fell for a LIO8, which I hardly use.
I had at home for evaluation:-
A Linn Klimax (supposed to be very good and looked nicely made)
A Resolution Audio Cantata (purely based on spec and styling)
A Weiss DAC2 (basic good engineering from a pro company at non-ctazy price)
I compared to the Metric Halo used as a DAC and as a Firewire-AES converter into the Goldmund.
Whilst I could probably tell one from the other on very specific sounds, the mechanical sound of piano pedals being used was a notable one, I would not be confident to identify any blind. If anything the Cantata was a tad clearer on the pedal sounds, and I liked its styling best, so I bought it.
As it turned out soon after I came across the Devialet amplifier since my local dealer was one of the first to sell them, and after trying one for a couple of weeks 5 years ago I bought it, so all separate DACs have been redundant since.
I have a Chord Hugo for portable use which seems very good too.