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

I used a Tandberg 320? and a Nakamichi zx7 for recording live choirs in the 80s along with a Tandberg 9000 R2R.  The DAT deck was superior.  However, the cassettes I made were of superior quality to nearly all prerecorded tapes.  There lies the probable cause for the previous posts.  Prerecorded tapes generally were awful compared to LPs and R2R 2 track or 7.5 ips 4 track.  Premium cassettes recorded at home or live sounded good.  I got rid of about 500 cassettes and kept only my live recorded tapes. 

Mijostyn-good for you, another audiophile interested in the music first although 78s can be very dynamic if frequency rangebound.  They are direct discs with perfect non-edited take credentials.  My 78s go back to 1900 so stylus size, speed and equalization make it more cumbersome to listen to.  It's an active hobby to listen to acoustic 78s (pre-1925).  

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.

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!