I can give you feedback on my direct experience with this question. The price range isn't as big as you would like but I've spent a number of hours trying to answer the question you raise.
Currently I own two CD players, one transport, and two DACs. These are a 1998 vintage Krell CD 250/2 (HDCD compatible $3200), Marantz SA 8005 SACD player ($1200), 1996 vintage Resolution Audio Quantum DAC (HDCD, $3500), PS Audio Perfectwave transport ($4000), and PSA Perfectwave DAC ($4000). I recently sold an Emotive ERC-3 Gen 2 ($450) that I also compared with these other players.
Here are my brief observations using my system of a Krell KRC 2 preamp, Krell KSA 300S amp, and Mirage M3si speakers with a Velodyne subwoofer. Since my preamp has a lot of inputs I've got all this gear hooked up all the time. All comments below are using standard Redbook CDs unless otherwise specified.
The PS Audio combination and the Marantz sound remarkably similar on regular CDs. I've compared them over a dozen times and I can hear a modest difference on some CDs and no difference on others. The PS Audio has a sharper transient attack on music that is recorded well but otherwise they both sound really smooth and musical.
The Emotiva and the Marantz sounded very similar also. On regular CDs it was hard to tell the difference. I think I could hear a smoother decay of instruments on sparsely recorded music on the Marantz but on regular old butt rock I couldn't hear a difference. The Emotiva decoded HDCDs but I sold it when I bought the Krell player since it does HDCDs also. I have over a hundred HDCDs so I need a compatible player.
I kept the Resolution Audio (RA) DAC because it does HDCD and I've got it hooked up to the Marantz as a transport. This is kind of nice since I can directly compare the DAC in the Marantz with the RA DAC on the fly. The RA DAC has a different character that is hard to describe. I hate terms like "sweeter" but it has a noticeable sound difference than the Marantz DAC. One is not clearly better than the other, they just sound different. If I had to describe it I would say that the RA sounds more like my turntable - it has a richer lower midrange. I could live with either one.
The outlier here is the Krell player. It does sound different than the other players. It's a little brighter in the treble (some might say "harsh") which stands out on some CDs. On some CDs I prefer the Krell but on others, particularly on albums that were recorded with hot treble, I prefer the PS Audio or Marantz.
I have several SACDs and CDs of the same music and I've compared them using both in the Marantz and using the Marantz as a SACD player vs. the PSA combo as a CD player. Results range from virtually identical to strikingly different. I've concluded that the recording and mastering differences on SACDs completely swamp the difference in players. IMO SACDs are a crapshoot. Some are way better than the original CD and some sound pretty much the same. The dual layer SACDs where the same mastering is used in both formats sound pretty similar using the Marantz and the PSA.
I have a 90's vintage Denon turntable with a Hana cartridge. I've got a bunch of music on vinyl and CD and I've compared a number of them. The music where the transfer to CD was done with care and compassion sounds good on both. All of my digital sources sound a lot like my turntable but the Resolution Audio seems to have the most similar character. However, there are CDs where the transfer was terrible. The digital version sounds much worse (compressed, dull, lifeless) as compared to the record. If one were to single out these perpetrators they could easily conclude that digital is inferior. IME it depends on the recording.
For me the lessons here are:
1. In no case does one player "blow away" another player. There are differences but I could happily live with the Marantz or PS Audio forever.
2. I would not recommend the Krell or another vintage player as one's only CD player. I think that digital playback has indeed progressed since the 90's.
3. I'm sort of sorry I sold the ERC-3 because that was clearly the value leader. I would really like to compare the Emotiva directly with a megabuck player to discern the difference. Maybe in a million dollar system there's a huge difference but I suspect that in most real world setups the difference would be subtle.
One more point. There is a huge treasure of wonderful music that was well recorded and lightly compressed from the late 70's through the early 90's including rock, jazz, and country. The best sounding CDs in my collection are mostly from this period. I am constantly discovering artists from this era that I hadn't heard. To say that all digital music is over compressed just isn't true. If you are limiting yourself to the late 90's forward you are missing the best recordings.
Currently I own two CD players, one transport, and two DACs. These are a 1998 vintage Krell CD 250/2 (HDCD compatible $3200), Marantz SA 8005 SACD player ($1200), 1996 vintage Resolution Audio Quantum DAC (HDCD, $3500), PS Audio Perfectwave transport ($4000), and PSA Perfectwave DAC ($4000). I recently sold an Emotive ERC-3 Gen 2 ($450) that I also compared with these other players.
Here are my brief observations using my system of a Krell KRC 2 preamp, Krell KSA 300S amp, and Mirage M3si speakers with a Velodyne subwoofer. Since my preamp has a lot of inputs I've got all this gear hooked up all the time. All comments below are using standard Redbook CDs unless otherwise specified.
The PS Audio combination and the Marantz sound remarkably similar on regular CDs. I've compared them over a dozen times and I can hear a modest difference on some CDs and no difference on others. The PS Audio has a sharper transient attack on music that is recorded well but otherwise they both sound really smooth and musical.
The Emotiva and the Marantz sounded very similar also. On regular CDs it was hard to tell the difference. I think I could hear a smoother decay of instruments on sparsely recorded music on the Marantz but on regular old butt rock I couldn't hear a difference. The Emotiva decoded HDCDs but I sold it when I bought the Krell player since it does HDCDs also. I have over a hundred HDCDs so I need a compatible player.
I kept the Resolution Audio (RA) DAC because it does HDCD and I've got it hooked up to the Marantz as a transport. This is kind of nice since I can directly compare the DAC in the Marantz with the RA DAC on the fly. The RA DAC has a different character that is hard to describe. I hate terms like "sweeter" but it has a noticeable sound difference than the Marantz DAC. One is not clearly better than the other, they just sound different. If I had to describe it I would say that the RA sounds more like my turntable - it has a richer lower midrange. I could live with either one.
The outlier here is the Krell player. It does sound different than the other players. It's a little brighter in the treble (some might say "harsh") which stands out on some CDs. On some CDs I prefer the Krell but on others, particularly on albums that were recorded with hot treble, I prefer the PS Audio or Marantz.
I have several SACDs and CDs of the same music and I've compared them using both in the Marantz and using the Marantz as a SACD player vs. the PSA combo as a CD player. Results range from virtually identical to strikingly different. I've concluded that the recording and mastering differences on SACDs completely swamp the difference in players. IMO SACDs are a crapshoot. Some are way better than the original CD and some sound pretty much the same. The dual layer SACDs where the same mastering is used in both formats sound pretty similar using the Marantz and the PSA.
I have a 90's vintage Denon turntable with a Hana cartridge. I've got a bunch of music on vinyl and CD and I've compared a number of them. The music where the transfer to CD was done with care and compassion sounds good on both. All of my digital sources sound a lot like my turntable but the Resolution Audio seems to have the most similar character. However, there are CDs where the transfer was terrible. The digital version sounds much worse (compressed, dull, lifeless) as compared to the record. If one were to single out these perpetrators they could easily conclude that digital is inferior. IME it depends on the recording.
For me the lessons here are:
1. In no case does one player "blow away" another player. There are differences but I could happily live with the Marantz or PS Audio forever.
2. I would not recommend the Krell or another vintage player as one's only CD player. I think that digital playback has indeed progressed since the 90's.
3. I'm sort of sorry I sold the ERC-3 because that was clearly the value leader. I would really like to compare the Emotiva directly with a megabuck player to discern the difference. Maybe in a million dollar system there's a huge difference but I suspect that in most real world setups the difference would be subtle.
One more point. There is a huge treasure of wonderful music that was well recorded and lightly compressed from the late 70's through the early 90's including rock, jazz, and country. The best sounding CDs in my collection are mostly from this period. I am constantly discovering artists from this era that I hadn't heard. To say that all digital music is over compressed just isn't true. If you are limiting yourself to the late 90's forward you are missing the best recordings.