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

There's no getting away from the harsh reality that vinyl is expensive. To acquire a second hand turntable that matched my streaming set up, cost the equivalent of $11,000 last year. Then I spent $4,000 more on upgrading it. No doubt, there'll be further expensive when the cartridge wears out 

That was an extravagance that I couldn't really afford. Yet I feel it was worth the expense. There's something special about listening to vinyl that streaming can't give me. I wouldn't want to live without it. I tried for five years and failed.

you can spend $7500-$10k on a table and it will outperform most streamers, it will definately outperform sub $7500 streamers IMO of set up properly.

The OP has stated

"so I have no reason to think there’s a setup problem."  

"Is this par for the course for this level of vinyl gear?  What do I need to spend to get my vinyl gear to match the performance of decent digital?"

@lousyreeds1 Within this Thread, there are contributors to the Posts that have thought there has not been a set up problem for their Analogue Source, but over time have discovered that much more can be done for the Source that does not break the Bank.

Using your own request "What do I need to spend" and my statement " does not break the Bank." suggests very strongly not much monies are required.

In the short term, there is a great deal that can be taken on board for free, about what are readily available solutions to isolate the Vinyl Source from being affected by energy transferral from the ambient environment the Analogue Source is set up in. 

Why is isolating the Analogue Source needing to be considered ? The reasoning for it is to create a Mounting for the Analogue Source that allow the Stylus when in the Groove to send info that is as accurately as possible a facsimile of the Groove Modulations. It is this energy sent by the Cantilevers to the Armature and Coils that generates the electrical current sent to be amplified and produced as the end sound through the Speaker. 

In most cases of a set up for a Analogue Source, there is energy getting transferred from the Stylus that is not limited to Groove Modulation, there is also an Adulteration of the Groove Modulation, caused by energy transferral as a result od the Mechanical Operation of TT and the shortcomings of the Tonearm.

Additionally, there is the Adulteration of the Groove Modulation caused by the Transferral of Energies present in the ambient environment. It is the putting measures in place to reduce the negative impact of the present energies that leads t the subject and practice of creating Isolation.

Usually Isolation is created from the Structure Designed for the Analogue Source to be seated upon. 

This then leads to the question, what has been done in your listening space for the audio equipment to alleviate concerns about ambient energies impacting negatively on a Vinyl Replay. 

If the info above is alien to you and the owned TT is Perfect Levelled with the Tonearm Optimised as the set up.

How much Adulterated Energy is being Transferred via the Stylus to be produced as a Electrical Energy and then become sound?

When making a decision during Sound Comparisons with CD Source vs Vinyl Source, how much of the sound being listened to from the replay of a Vinyl LP, can it be said 'hand on heart', is the sound solely generated from the Groove, Modulation?

I would like to think others with experience 'chip in' and confirms the selecting a method as a supporting structure for the TT, has the benefit where substantial improvement in produced sound can be detected.

At this stage everything on offer remains without a cost, which must be an attraction.          

Try to get your hands on one of those optical cartridges from DS Audio...best i've ever heard vinyl sound anywhere seems to be from it....

Sorry to hurt your feelings, but, it still can't keep up with high end digital audio...it should be obvious where the bottleneck is.

But, my primary use case is a bit different, i'm in the process of digitize/salvaging stuff from old obscure long gone artists whose music might also get lost forever.

Did you mention you have a phonostage? I didn’t see any mention of one. So if you’re using a phonostage that’s internally contained within the turntable, then that could easily be why your digital setup sounds better. I find that most people, listening to popular music as they do, will think digital surpasses vinyl. But listen to a recording of a flute (an instrument i play), or any other well-recorded acoustic instrument and you will hear the difference between the two more easily, and I wouldn’t be surprised if the vinyl sound was closer to how a real flute sounds. Of course, that begs the question of how many listeners KNOW what acoustic instruments sound like. I get the impression that’s not the case. I mean, that the majority of people’s music is acoustic. Even if that, the ’80s produced the worst vinyl - and sound - of the 20th century. Vinyl was so thin you could flex it easily. NOT the case with an lp made in 1960.

So, If you are listening to  classical, I can imagine the vinyl sounding better. But if you listen to pop, rock and the rest of the musical genres, then I could see digital sounding better, since so much music is overly compressed and manipulated.

What do you listen to?