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

The average high end Vinyl rig 
with cartridge and power supply is at least $5-6k. That being said 
a Lampizator has a Tube rollers dac for $7k  , then buy the critical 
Final touch audio - Callisto USB 
cable  and it will not only give a Vinyl a challenge but beat it in many areas even 2x that. I have listened to many record rigs side by side , band width is very limited to 12 bits , where digital can go 
to well over 20. Plus you can keep your labor of cleaning,demagnatizing, pops and clicks, cartridge maintainence, a wall just to store them . Where with 
well done Digital ,your whole library at the touch of a button through a tablet. I owned a Audio store in the U.K.  What’s next a stack of 45 records stacked on a spindle like In the days of old ?
why not buy a juke box too ? As I suggested check out a Very good Vacuum tube Lamoizator dac 
and get a good power cord and a Essential top quality ASB cable 
such as the Final touch Callisto 
the best cable outthere under $1500, for $800 is a steal,
Digital owners ,just check it out.

If you are currently a "vinyl" person, then you may have an expectation of a sound that digital .... well just isn’t.

It should not be about "vinyl" or "digital" persons. It should be about high fidelity, getting as close as possible to natural sound of instruments as they sound in nature. But this is what most "vinyl" persons are telling: it sounds more natural.

I have posted before on this topic, so I’ll be brief. I believe that 90% of the problems in ANY sound are locked into the recording/mastering process, and maybe the actual pressing with Vinyl, since there is so much opportunity to f it up.

There’s another thing which makes things much worse than they should be, which is room acoustics. However typically when you have a problematic acoustics in your listening room is when you usually get bothered with the subject. One doesn’t have to be aware his biggest issue is room acoustics, though. It’s what makes good recordings sound less good than they’re capable of, and it can make worse recordings sound unbearable instead of still enjoyable.

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. 

35 yrs ago I had a fully vinyl rig set up to compete with a heavily modded magnavox player du jour (which did sound way better than other players of the day). I had many vinyl/CD repeats and auditioned them extensively, one after the other (through a big tube amp & Vandersteen 4 speakers). Digital always sounded different from vinyl in way described above, and to my ears, vinyl usually sounded better. But it was easy to see the vinyl recession that would follow--vinyl would no longer be ascendant. 

I formed an opinion then that still holds up, though my audio gear is vastly different today: that is, if I had a vinyl system, I would put serious $$ into the TT & cartridge, also the phono preamp--because the extra outlay could be heard relatively easily. But with digital, I would keep it mid-level, never plunging on the big-$$ brands of the moment. Beyond making sure the cables were good quality, I'd upgrade players from time to time, rather than going for any one SOTA player.

And so it is today in my desktop audio system. No vinyl here (no room). I use DACs pretty much as I did CD players back in the day. I'm fond of non-oversampling (NOS) multibit DACs & am on my 2nd. Its sound is very fine for digital (MHDT Labs Orchid @$700). I have no urge to upgrade. My passive studio monitors are very high resolution & sound wonderful to me in the current setup. I listen to a lot of streaming music, also 100s of GBs of music I ripped to the HD.

One thing I would certainly try if I had a vinyl front-end (1500 LPs in storage) is to rip vinyl recordings to disk, then output through DAC + speakers. That would be very interesting, to see if the positive attributes of vinyl survive digitization.