How much do you need to spend to get digital to rival analog?

It all depends on what sounds better means. There are obvious differences when you compare analog to digital versions of the same recording which I love to do with people. Frankly, it goes both ways. Sometimes the analog version sounds better and sometimes the digital version sounds better. I have to believe it comes down to how the recording was mastered or remastered. I have never had an instance where a CD sounds better. But with high res (96/24 or higher) digital downloads it is a toss up. Dylan's Desire sounds better in analog using the MoFi 45 RPM disc. Early Bowie stuff sounds much better in digital even though they were analog recordings. Much of the very current recordings sound better in digital form such as any of the recent Wilco discs. This is all by direct AB comparison with both versions running at the same time with the volume equalized by meter. I use an Apple Mini loaded with the Pure Music program. I love vinyl but it is just not true that it sounds better all the time. It does sound better much of the time and I have many great old records that I have no desire to get a digital copy because the analog sounds great. But, I do have some knock out digital recordings like the high res version of Tool's new disc. WOW.

True atdavid. Nelson Pass admits to adding harmonic distortion to his units because "audiophiles just want to be happy." I prefer my bass a bit on the heavier side because I feel it makes things sound more live. If I turn my Sonos speakers on in the rest of the house it creates the effect of being in a much much larger room which with concert DVDs is a lot of fun. Accurate? What is accurate? Speakers are such defective devises, even the best ones, that there really is no accurate. In reality it is pleasing vs not pleasing and pleasing is a matter of taste. Yes, the really best systems always get big smiles because relatively few of us get to hear them under the best circumstance (not at a show). So when we do it is big wows. When it comes to evaluating these recordings a lot of issue give the impression of "better." In the case of the early Bowie recordings the remastered recordings are hugely better obviously because of the mastering. The digital versions are more dynamic and the bass is more up front. Dylan's Desire sounds better in vinyl because it is smoother and has more "air" in it. The digital version sounds harsh in contrast. As a rule vinyl versions in my system have more of that "air" effect which may be a euphoric quality of vinyl or my record playback system. Setting up a top notch vinyl playback system is not easy and it may be that the digital only group might have had a bad vinyl experience. The only excuse I can find for the vinyl only group is that they are a group of recalcitrant snobs:)
(that is a joke guys. Then again my mother use to say the truth comes out in jest)

As you suggest Mike Stereophile did this interview back in 1995. I remember listening to the very first Sony CD player at a friend's shop in Akron, Ohio through Krell electronics and Magnapans. It sounded pretty poor. But, cassettes sounded a lot worse and people flocked to them because they were not vinyl and you could play them in your car. CDs were even more convenient and had the potential to outperform cassettes, were not vinyl and they would soon be playable in car audio systems. It was obvious they were going to take off whether or not audiophiles like them. After all we are a very small proportion of the market. Now it is MP3 downloads. It would be three years before Accuphase would make a CD player I could listen to. I suspect it had a fair amount of harmonic distortion added in because it was very tube like.
Still, the best records had better dynamic range. Then came the volume wars (dynamic compression) which IMHO ruined the sound of most popular CDs. Fast forward to High Res digital 96 or 192/24 PCM and recordings that were mastered for this and you have a whole different ball game. Even old analog recordings that were remastered in digital can sound fabulous. In many instances it is only because the original master was poorly engineered. But, better is better. 
The normal background noise on vinyl excluding the rare scratch or loud pop I find not to be objectionable at. It is dithering your brain and in some ways, believe it or not makes the music more realistic. When have you been to a concert with no background noise? Never. People talking coughing, shuffling around, chairs squeaking and the -ss behind you that has to whistle after every song. Vinyl is actually quiet in comparison!
The quietness of digital is actually spooky, sterile. You know you are listening to an artificial recreation because there is no noise. Is this one of the reasons I prefer live recordings? Maybe. 
There is more behind this than the technical aspects and this issue is highly multi-factorial. Gross characterizations do not work and anyone making them has a hidden bias. 

Mike, I have not yet spent nearly as much on hi fi equipment as you have but my system is no slouch either. Neither the physical reality or my own listening experience matches yours. The best your ever going to get from a record is 70 db. Most are down around 60 db if they have not been damaged. With 24 bit digital 110 db is attainable limited by digital max.
But, as with everything we listen to it all depends on the mastering. Digital is going to sound very flat if as usual today a ridiculous amount of dynamic compression is used. Everything we listen to has been mastered, engineered. The older records were mastered assuming the limitations of vinyl. Dynamic compression was used to keep the music above the noise floor and below the maximum reasonably attainable tracking capability of phonograph cartridges giving at best 70 db of dynamic range. If I use that same master on any current full resolution digital format I will get the same 70 db dynamic range. If I make a master for digital use only with a dynamic range of 90 db I can get considerably more dynamic range out of any of the high res digital formats. If I used this master on vinyl the stylus would fly out of the groove. These new masters and remasters are starting to invade the market thus hi res digital can easily attain the dynamic range of high speed reel to reel. 
I can hear and demonstrate this easily with my system using the right software which means I can do it with yours. Which means you can do it also. I can also fool people into believing a version of a recording is more dynamic in AB comparison just by tweaking the volume 2 db. 
In the end it all comes down to the master and then the limitations of the format and although many analog to vinyl recordings do sound better than their digital counterparts, analog media are crippled when it comes down to dynamic range even next to lowly 16/44.1  https://en.wikipedia.org/wiki/Comparison_of_analog_and_digital_recording  
So Mike, it appears you have an obvious bias in this regard which makes it difficult for us to interpret what you have to offer in this conversation.

Sincerely,
Mike

Mike, I was not trying to attack you. Sometime we do not realized how other people hear/read our words and I was just suggesting, "it seems like, or appears" I gave an example of digital remasters of old David Bowie records that sound much better than the original analog audio in direct AB comparison with volumes matched (EXTREMELY important). I do believe this is because the original masters were poor not due to any defect or superiority of these formats.
Yes, originally digital was touted as this, that and the other. We audiophiles were scratching our heads wondering with all the theory what went wrong because it did not sound so hot. Several decades later most of the problems have come to light the big one being that you have to master in a different way to suit either analog or digital playback. Done correctly without dynamic compression and with playback no lower than 96/24 I know that digital can provide state of the art results in particular with live recordings that have the inherent background noise of a live situation. Right now I am listening to the MPS re release of George Duke's Faces in Reflection. Analog all the way and wonderful. 95 dB and I feel like the band is right in front of me.
Raul, I love the analogy of our brains being ADCs. They are!
Atdavid, there is always a reason and searching for that reason allows us to fix problems instead of compounding them. 
In a nut shell some of us think Analog is inherently better and some of us think digital is inherently better. Some of us think it depends. I will place myself in the third group with the caveat that ultimately digital will prevail.
It allow us to do things that are impossible in the analog domain like room control and seamless bass management. It allows us to go online and download music in a heartbeat to the most efficient form of storage, a hard drive now in 24 bit formats w/o lossy compression. If there are any detrimental sonic artifacts left they will eventually be banished and Mike L will sell his analog stuff to the Smithsonian for display with the Write Brother's Flyer and other Dinosaurs. I'm a hopeless romantic so I will hold on to mine:)

Everyone has to remember that now it is the rare recording that is done analog. The vast majority are now recorded directly to a hard drive. So in saying that analog is better you are also saying that high resolution digital is not a problem and that analog playback of digital material is better than digital playback of digital material. I believe this is an admission that vinyl playback is adding something to the signal that many audiophiles prefer be it the background noise that dithers our brain or increased distortion (added even order harmonics). There is a euphoric quality to vinyl playback. Another interesting comparison is older analog recordings vs newer digital ones, a very difficult comparison to make because you can not get a single piece recorded both ways for comparison. In thinking about it I really could not say. Most of my classical collection is analog and given that I was very picky looking for the best artistry along with recording quality, it is an excellent collection. But, what little DDD I have is also quite good. I have the four Brahms Symphonies in 24/96 digital and they are wonderful. I can not imagine it getting any better. But I also feel the same about many of my analog recordings.

Comparison's made with the same system cancel out everything except the variables being changed. For digital it is relatively simple. It is all about the DAC. Any good transport will suffice. For Vinyl however it is the cartridge, tonearm, TT and phono amp. Get a few of your favorite albums in as many formats as you can. In order to do this correctly you have to be able to match volume levels and they have to be exactly the same which is not so easy and you have to do this with every set of recordings. I use a sound pressure and match peak output. Then I get all three going, CD, Hi Res and vinyl just a little staggered so I can listen to the same passage in all three formats, sit back and trigger between the formats with a remote. This is actually a lot of fun and I promise you will be surprised at some of your results. The first time I did this was with Dylan's Desire as I had all three formats and I was sure the Hi Res was going to trounce the others. It did not. The MoFi 45 rpm version won hands down. Even Cleeds would agree. But in other cases Hi Res won like Led Zepplin One Two and Three. The surprise here is how well vinyl matches up to Hi Res. You would never think that dragging a rock through a trench could match up against modern computer wizardry. Anyone who thinks taking care of records is a PITA needs to bone up on their technique. Even getting up to change sides is an advantage if you are over 60. If you sit too long in one place you freeze:) With an automatic tonearm lift you do not even have to disrupt whatever other activity you have going at the time. Everyone should know my mantra by now. Dust Covers and Conductive Sweep Arms. 

Yes zalive, it comes down to the master. But better is better. We have no control over which master is used. 
The question is, is computer audio better than digital playback from a CD drive. I can not really answer that question. I have compared the original CD to its copy on a computer (Apple Mini with Pure Audio) and I can not tell the difference and the computer is up sampling to 192/24 the player is not. A down loaded Hi Res version does usually sound better than it's CD counterpart but again are they using the same master? 
I am more than happy to get rid of all my CDs. They are now all on the hard drive, what a PITA that was. Gives me more room for records:) I have nothing bad to say about computer audio. I love the degree of flexibility you have with Pure Music which uses iTunes library to organize the music. The whole set up cost me about $5K. The Mini, a 6 TB hard drive and a Berkeley Alpha USB. This is about the price of my cheapest cartridge so from a price perspective digital has it all over analog. 
I only buy a CD on rare occasion when music I want is not available to download. 
Geoffkait with two F's, Michael Fremer's opinion is not one I would rely on. His hearing is way better than mine and your's for that matter. He can hear the "dramatic" difference between a $100K turntable and a $400K turntable. His use of superlatives boggles the mind. I can't even tell if he likes music. 
Geoffkait, I'm worried about your ears. Cassette tapes suck. I have a Nakamichi Dragon up in the attic you can buy from me if you like. I bought it to record cassettes for the car before CDs became available. 
I'll bet you are an 8 track fan!
Fleschler, I only have 2,348 78's  

Uberwaltz, I am thrilled that you like to watch little reels go round and round but even under the best circumstances cassettes are colored and bland. If you turn the dolby off they sound better but noisy and the worse kind of noise is the steady state stuff like tape his. There is no way you can win but back in the day it was the best way to get music in your car and in a way they are better than CD's because they are harder to damage. One good scratch in the right direction and a CD is worthless.
Played back on the Dragon they are worse than MP3 files. If you like to listen to then for nostalgic reasons wonderful, that is why Howard Johnson's made 23 flavors.

I am full of preposterous blanket wet noodle statements and totally politically incorrect which is intentional.  

Mikelavigne, I totally agree, it all comes down to the master. I also can not tell a difference between vinyl and a 192/24 version done with Pure Vinyl of that very same record. I am debating getting one of their phono amps but have not made that leap yet. The Hi Res files files I buy are usually old material I already have because they have been remastered such as older Bowie discs, the older Stones records etc and the remasters have universally been improvements over the older versions. Occasionally a new record will come out in Hi Res. Several groups are allowing this such as King Crimson, The Shins and Wilco. Obviously I have no old recordings to compare these too but they are all first class projects all the way through and they do sound better than your usual CD and dynamic compression is used much more sparingly so they are as or more dynamic than an LP.

Room acoustics are extremely important but that avoids the question. Given the same room and system how much do you have to spend on digital to equal the performance of a $3K turntable. I do not know if that includes the cartridge and tonearm but say it does which means it is not a very high end table. It would be one of intermediate performance. You could probably beat it with a $2K computer and usb interface. That does not include the DAC but the turntable does not include the phono amp. 

I already sold all my CDs except the special ones like my RT personally signed copy of Shoot Out the Lights. I downloaded them all to a hard drive and sold them to Bullmoose Records for store credit which I turned into records:) It took I think it was two months and 6 trips to Bullmoose. Now I have all that room for more Records and another 4 TB left on the hard drive for Hi Res downloads. Does life get any better? I think the JVC Direct To Disk LP are as good as LPs get not that there are not others out there particularly in the classical realm. I was never big on Telarc disks mostly because I had versions of all the stuff they did by artists I liked better. High quality recordings are no good if you don't care for the performance. The first popular digital recording was Ry Cooder's Bop Till You Drop. Great music but is is missing a little of the sparkle the best recordings have.
Thanx again atdavid for clearing the air. One other comment to add is that negative feedback is not the big bad boogeyman. Done correctly it is vital for some designs and "no feedback" is not necessarily better. 
Mahgister, theoretically you are right but sometimes you have to make compromises and testing a rig in everyone's home is not practical so you can only say, "in this room with this system." Frankly, all of use are guessing based on our experience. In reality I can't even comprehend the question because my turntables cost a whale of a lot more than $3K and my digital playback system cost less than 1/3rd of my cheapest turntable.
I'm guessing again but I would say when it comes to serious listening digital and analog get an equal share of my attention. I am also not picking out the music based on sound quality but because it is the music I want to hear at the time. If I were given the opportunity to buy an older analog recording in remastered Vinyl or Hi Res digital I would try to go for the one that I though sounded better. If I can't determine that I just get them both:) I also think it is obvious that digital is a much better value than Analog. It takes much less money to get to a near SOTA set up. 

Geoffkait, My old Nakamichi Dragon is in a box buried under a lot of other boxes up in the storage room right where it belongs. To compare cassettes to Hi Res digital is like comparing moonshine to Remy Martin XO. 
Zalive, if you do not like the symbals on digital recordings just focus on the bass.
Mahgistar, exactly. So my solution to the problem is just have them both then you can decide for yourself. In my experience...it depends. 

Gallus, priceless.
Zalive, I can still hear fine up to 18 kHz.  I have had many issues with CDs over the years I suspect to various problems with links in the chain.
It is obvious from many albums such as The Trinity Sessions that digital recording can be excellent. I suspect it is the playback process that creates the issues you complain about. Having evaluated many recordings of which I have versions in both digital and analog formats I can say without question that in many circumstances the analog version sounds nicer due to the addition of euphoric distortions. When compared to live acoustic instruments the digital version is more accurate. In many instances that sense of air and depth that many of us, myself included like is due to added distortion. Many interpret that "air" as high end. I have many remastered Hi Res recordings (downloads) that over come the lack of euphoric distortion through thrilling dynamics and more accurate imaging. 
Making generalizations about any format is a mistake and more likely indicates a bias on the part of that individual. There are just too many steps along the way that when not done correctly can pervert the final product in any format.

Mike