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

Then send the Dragon to me.
We all have opinions obviously but you should avoid silly blanket statements that you cannot substantiate.
Sorry but I do not watch the little reels spin whatsoever, too absorbed in the sweet music.
No nostalgia involved, just music on a grand scale.
As I said I invite you to listen to them on my rig......

To the Op's question - as it applies to New Music sourced from a digital file going to vinyl.   

I talked years ? ago to a few of the studios that do the vinyl cutting near where I live. Its a well known fact that the engineer when supplied with higher resolution files from the artist will use these for the actual vinyl cutting.

So, to the Ops question in regards to...... new music on vinyl - a DAC that will play 24-96 khz - on average is the requirement to match the vinyl record.

With that I personally have heard 16/44.1khz  CD's , per my previous posts here, whose source recording / mastering was done so well that it was - right there. Likewise, some Hi Resolution files sounded like Ka Ka - due to I assume - poor recording technique. We are at the mercy of the recording. 

https://vinylpressing.ca/pages/vinyl-pre-mastering

Vinyl Pre-Mastering - taken from the link. 
 
Pre-mastering is the process of getting your audio ready for the vinyl lacquer cutting stage. If your audio is already mastered for vinyl, you will not require pre-mastering services from Train Records.

What is required for submitting an acceptable vinyl premaster to Train Records?

Source Audio Files:
• 24 bit 96kHz WAV or AIFF format file is the vinyl pre-master standard. Other file resolutions are acceptable, down to CD quality audio, 16 bit 44.1kHz
• File resolution should be the highest available, but should not be converted up to a higher resolution.
• MP3 audio is not a suitable source for vinyl production.
• The source audio files should be provided as a single WAV or AIFF format file for each side, with track spacing as it is intended to appear on the record and with an accompanying PQ sheet, indicating track IDs

A Note About High Frequencies:

The lacquer cutting system (the next step in vinyl manufacturing) is capable of putting very high peak levels on the record, but only ideal playback systems in optimal conditions will be able to play the sound back without distortion. Since we need the record to be playable on all types of equipment, it's necessary to limit the High Frequency information. It's recommended to provide a vinyl premaster that already has a balance of high frequency suitable for vinyl production.

A Note About Low Frequencies:

Excessive level in the very low bass can cause the record to skip. Excessive stereo information in the bass appears as vertical movement in the groove, so it's sometimes necessary to remove the stereo component of the music as well as any out of phase information in the very low frequency range. The cutting system is equipped to correct minor issues with the bass however, more severe problems will result in a record that can't be cut or that sounds very different from the source audio files provided. It's recommended to provide a vinyl premaster that already has low frequency level and stereo content that is suitable for vinyl production.

Fleschler.
I will grant you that were indeed a number of poorly recorded tapes sold, but so too CD and records.
There were/ are some superb pre recorded tapes as well though but yes generally a very well home recorded tape on say TDK SA media on a top flight Nakamichi deck can sound spectacular.
As good as same treatment on a good r2r? No of course not but nothing like Mijo blanket critique.
If his Dragon truly gave such poor results it obviously needs a full restoration!

@mikelavigne
Hello Mike,

...he heard tape and vinyl do dynamics far beyond what any digital could do

I am perplexed at the use of the word "can" because digital, esp hi-rez, *can* do dynamics (i.e. the difference between the lowest & highest amplitude reproduced) beyond what analogue *can* do.
Whether the files contain such dynamics is another matter, of course -- in my experience, they often do not! In fact, much of the digital content available today is abysmally compressed. Additionally, the digital compression rate is much higher than we find in LPs. compression, I believe, is one reason why vinyl sounds better: because the source material is better, to begin with.

In this respect, it is not surprising that an LP in your system has better dynamics and generally sounds better than many (mediocrely mastered) digital files.

Following up on @ct0517 post above, I have compared a vinyl reproduction to the same LP encoded 20/192 (direct from the TT output). The playback results in both digital & analogue were not particularly different; being of a certain age, I like the analogue sound—but frankly, I cannot say the digital copy sounded bad in any way (in fact, I'm not sure I could easily tell the difference!).

@tzh21y
As to the original question:As mentioned before, the answer to this depends on certain variables, but to simplify things, let's assume an excellent quality LP and a similarly outstandingly mastered digital counterpart and an outstandingly well set up TT with a superb sounding phono.
In my experience, you would need in excess of 3k for a high performing dac, a reclocker, and a very good music player & suitable cabling in between.