How much do I need to spend to make vinyl sound better than digital?

$5,477.36

There is no simple answer to your question.  My best phono playback system (I have more than one) has a price tag of over $70K, my best cd player cost almost $17K.  Usually, the phono playback is the better of the two, but not always.  It depends of the recordings, how they were mastered and so on.  It is safe to say that the best bang for your buck is digital.  Chasing the elusive best sounding recording, whatever it is, is like chasing after the Holy Grail.  

$5,477.36 Yep that’s exactly what I came up with too. Great work middlemass.

Phonostage, phonostage, phonostage- don't forget the phonostage!

$5,477.36 including taxes and tariff charges is about right. Using  a significantly better phono pre and cart wil keep you content until you're prepared to spend another $5477.36 for a nice table/arm.

I think that @tablejockey is giving some good council.  Let's say you decide to pull the trigger and upgrade your table & cartridge.  Surely you would want an external phono preamp.  Why not add the phono pre now and see if it gets your system closer to where you want to be?  If that doesn't get it done, then you have a phono pre to upgrade your table around.  There's tons of great phono pre's out there with all kinds of different sound signatures.  Good luck and cheers.  

buy a set of cheap speakers. 

hook it up to your digital chain.

you are done. 

The issues you describe sound like it could be a less-than-optimized set-up.

My guess is that if you haven’t spent the time to fine-tune your table set up, then that’s where I’d start. Now, perhaps your particular model doesn’t allow for much fine-tuning, which would be a related issue. Nevertheless, if your cartridge isn’t perfectly aligned and sorted out together with your arm and table, then you’re not hearing what your rig is capable of.

I’d start there.

You’ll learn more about how it all fits and works together. There are various tools that can aid you. Do all that before investing in a new anything. Then, from there make a call.

Vinyl is an incredible medium but it takes work to optimize it.

These results are inevitably some combination of: 

• You might simply prefer the tyically "clean" sound of digital
• The kind of music material you enjoy has generally good mastering quality on digital; at level with or better than the vinyl alternatives
  • I enjoy a lot of 60 - 80s pop & rock - and this material fares much better on vinyl, IMO (on average)
  • Some of the 1990s+ Redbook CDs I have from Japan sound just as good as vinyl
• Poor isolation. A good headphone setup can reveal if that’s the problem or not!
• Your analog rig might not be that great. It could be one weak link in the chain, multiple pieces, or a bad match between anything. That said, if the above factors don’t swing you to vinyl, then there’s little point in spending gobs of time & money to improve your vinyl chain. 

And yet another opportunity for one of my favorites:

Typically, these days you can equal things by carefully choosing and investing about the same amount as your analog rig. For me my digital and analog sound simply stunning and the same... as I desired. You can see my systems under my userID.

For systems that are more budget oriented, sometimes you may need to spend a little more on digital... say maybe up to 20%. But this is changing rapidly. 

So roughly: Turntable + Phonostage = Streamer + DAC. 

You have to put the same effort you would into choosing a TT, cartridge and phonostage into the Streamer and DAC. My rough rule of thumb for a digital system is 30% speakers, 15% amp, 15% preamp, 15% DAC, and 15% streamer, 10% cables and interconnects. Really generally. Same for analog 15% TT and 15% phonostage. 

It can't be done. You could spend $100K on the most esoteric turntable, cartridge, tonearm, base, cables, and phono stage, and its potential sound quality will never equal that of spending $10K on a network player/streamer and DAC. It just is what it is.

Phono stage is extremely important.

Some Japanese CDs do sound relatively good, and my old CEC TL5100Z player is not too bad, but vinyl always sounds better with Nottingham table, often much better.

I no longer see the point of bothering with vinyl unless you have the funds to go first class with both vinyl and digital. A first class digital setup will not have you longing for vinyl so why bother. Now I can see going for the vinyl assuming one has both the funds and a large vinyl collection. I have around $25k in my vinyl setup, over 3k albums and rarely play vinyl.

ONE. MILLION. DOLLARS.

Seriously though. Despite what @ntpc4 claims (and baseless generalizations like that suck anyway), my $60K analog front end still completely smokes my $16K network streamer every day of the week. It’s not even close. :)

Vinyl sounds so good on my system I rarely even bother with digital, unless I want to audition some music I might buy on vinyl, or I want to play music that was recorded digitally in the first place. Vinyl for me is just about always more satisfying for listening to music. But I've been doing it for a long time, and have some 5000+ LPs.

Vinyl can never sound like SACD on a good player 

Before you spend any more, ensure your set up is spot on. If you aren't comfortable doing this yourself, enlist the help of someone who can. Pay them if you have to. Making sure you have that last ounce of performance out of your current rig can help you decide if you want to go further.

And I also agree with comments regarding how important the phono stage is.