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

Picking a CD Player / DAC

1) Pick 3 music selections that (a) push your buttons, (b) make you come alive. (c) are like a fountain of youth for you. These selections will be different for each one of us and they should not be longer than 15 minutes in total.     
                                                                        
2) Take your personal CD player or DAC to 3 different Dealer Salons or friends places.                                                                     

3) Insert your CD Player / DAC into the chain first (very important) and listen to the music. This allows you to "Form An Opinion" in their "Room" with your gear and music as input.                                

4) Now - try the music with their CD players, DAC's, ...                     
If they allow you to bring the gear home - highly unlikely - even better.

If their gear, does something better for you - then you know what gear and the cost.    

3 music pieces and 15 minutes of music is important.  I found more than 3 was too much to take in. Also 15 minutes allow you to be out of their hair within the hour (if at a Dealer Salon)  

I think the technology of the 20th century, dictated that a recording engineer knew the limitations inherent in vinyl.  
They knew that the music being recorded was going to be mass produced and the majority of sales would come from LP's. And the turntable was the main source for playback. It's no wonder music from the 20th century sounds good on a turntable.

I agree that most analog system sound like music being played not a recording of music. Is this because more information is being stored in vinyl than on digital? Can we even measure how much information is stored in a LP record?

Even though the LP's can sound more "real", I don't care for all the maintenance required. It's like owning a car, every time you operate it you are wearing it out.  

Hi  tzh21y,
In response 
"I have been used to analog my whole life "
Specifically what kind of analog set up do you currently have? forgive me if you have already answered that.

" I think I read someone said that "no digital will ever satisfy like analog" "
But at what cost are you willing to see if digital could make that happen?

When ever I feel comfortable enough to confess to people that I am a self proclaimed audiophile, they ask me "what kind of turntable / analog set up do you have"?,  I answer I don't have one. 

They then ask me "why not"? and I say " because I can't afford it".

You may need to reevaluate your situation and priorities in your current situation. Cherry pick your LP's and if $3k is your number, stream the rest with a decent player,  while simultaneously growing your LP library 
- Best of Luck ...

It costs me about $12....... for the right CD.     So many times the better format is simply the one that was from the better master.... or better Mastering.  I've have good and crappy versions of the same record in either format.  I love both LP and CD, and there's good & bad versions of each.  HiRes digital..... when DONE RIGHT.... can beat them both though.  I'm still too afraid to get into HD though, because some HD pop music is still over compressed, and there's no return policy if your not happy with the sound.  I wish I could get a refund for all the defective CDs i have, where the sound is distorted.  That should be a legitimate defect.

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.