Good points by all. Some musicians want top notch instruments, others will perform on whatever is available and adjust their style. If any piece of equipment does something you really like, and you can manage the cost, then get it!

James Booker made some recordings at Paramount that have now become an album called The Lost Paramount Tapes. Apparently they had a bunch of great pianos for him to choose from, and he chose a little spinet that was just a set piece. In the eyes of the producers this amounted to James ruining the entire session. When I listen to those tapes it’s obvious to me that James knew what he was doing. There’s nothing inferior about a spinet. It’s just knowing what to do with it.

One of my favorite memories was a PBS concert back in the 1980s.  The concert featured a famous flautist who was interviewed by the PBS announcer after the show.  The interviewer handed this flautist a cheap plastic recorder and asked him if he could play a tune on it.  He made incredible music with that toy.  I was amazed.  It’s true:  95% talent and 5% instrument.

From my experiences it was easy to hear differences between under $500 DAC and $1k or higher. And the differences manifested themselves in the detail of the playback. BUT this was not the case with the grouping of $2k to $10k DACs. The only thing I was able to hear with this wide range of gear was a quieter blacks / lower noise Floor.

How easily can you distinguish between different DACs?

It depends. Listening for differences on any component will not be obvious or even heard if there are no room treatments in place and also the quality of the rest of the system.

@ghdprentice 1st post makes good sense. Quick a/b comparisons are not really helpful. Best is to ignore measurements and listen to a DAC for a week then swap over and  listen to the other for a week and you'll easily hear which one brings more fun and enjoyment.

Starting to appear on these forums is the idea or reasoning that all new DACs including the cheapest are better than anything made more than 10 years ago (some even say more than 5 years ago) This is abject nonsense.

I have a 30 year old Wadia 15 that plays redbook only and have been biased in the opposite direction. That is to say I have been expecting to find something to equal the Wadia's wonderful redbook quality but also with hi-res capability and the convenience of USB etc. etc.  I have listened to a few including the stratospherically priced dCS and still own the Wadia. I certainly do not buy according to measurements. I do not have specs. of the Wadia and I have no desire to obtain them. I'm sure a cheap Topping will have specs an order of magnitude better but have you ever heard one in a decent system in a room properly sorted acoustically? I rest my case, it weighs 15Kg 😁

I'm sure the Wadia is something special, however the state of the art in digital audio has progressed since then.  I was using my ARC CD player from 2006 up until the beginning of 2021.  I thought it was a good redbook player until I heard my new DAC/Transport in my system.  The sound blew me away.  Until then I had no idea CDs actually had so much detail and resolution built into them.  The music from my new DAC was sensational.  Before, I would listen to one or two CDs and then switch to vinyl.  With the new DAC/Transport I listened to CDs for hours.  Then I got a streamer and my whole music world opened up to millions of songs.  It's been quite a journey.  Good thing I retired because I might never have made it back to work.  

I just recently upgraded my DAC.  Same brand but moved to their top of the line model.  I gained sweeter highs and stronger bass with more resolution.  The bass has texture and detail that makes listening even more intriguing.  Do DACs sound different?  Yeah, they do.  They do by a lot.