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

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.          

Cartridges, Tonearms, TT's can be discussed for evermore, but if the Trilogy are set up to function in an environment that is to the The Trilogy, equivalent to a Person using a Jack Hammer, there is nothing to come downstream that will fix the problem if the Volume Control is set to the above 0 Setting.

What goes on upstream of the Speaker is not sound, it is merely an electrical flow, the end sound comes when the electrical flow moves on from the Speakers Xover.

Speakers are known for their adeptness at presenting a sent corrupted signal as a   corrupted sound. Add a resolving upstream system and the Portable Radio's Sound will be not too far from making a good impression as the comparison to the sound produced from the audio system.

People are so in tune with the notion of the importance of a high quality foundation, but when it comes to preparing for a Stylus to do its job, the notion of the quality foundation slips the mind of many.     

Listening to Recordings that are easily identifiable as being quality recordings does add to the experience of listening, there is the impression made from the Sound being produced as well as the knowing not much better can be offered from the Source Medium. 

Unfortunately to experience LP Albums produced on the Vinyl Medium can be quite costly in todays market, to buy into the Albums for a user of a Analogue Source. Buying used Vinyl LP's, also has its Pitfalls and not every user of Vinyl on theor Analogue Source is going to know their used item purchase of a copy of the Best Album of a particular recording is actually one which is a poor copy due to the used condition only?

For myself I have Vinyl LP's in use that are with a condition that adds to the experience of listening to a recording on a Vinyl LP.

The condition being referred to is Cleanliness, (Purification) of the Source Medium being the Vinyl LP.

I have owned Vinyl LP Albums for numerous years ( in some cases Albums are owned for near 45 years).

Over the years as my interest in being in control of the smaller things in enjoying audio equipment to replay recorded music grew, I developed a discipline for Cleaning Vinyl LP's, along with some other cleaning disciplines for audio related items.

Not too long ago, I adopted a New Design for Cleaning which has become my only cleaning method. It is a manual cleaning activity using a purpose produced solution and has superseded my usage of US Cleaning and other Solutions used over the past years for manual cleaning are no longer considered as a cleaning method, or no longer are recognised as a Cleaning Method.

Whilst I have the capability to do the manual cleaning task without harming the Vinyl LP, I will remain using the PAVCR Manual Cleaning Method using the Solutions designed within that are available to me in my Country.

The PAVCR Manual Cleaning Method, when carried out closely following the guidance given in the document, does one thing as the end result.

The one thing that is achieved as the end result, is a Vinyl LP that when used to replay the recorded music, has a new and very noticeable quality when it is being replayed. The new quality that is undeniably present is one where the Cleanliness of the LP becomes audible, there is a strong sense imparted, that the medium in use is one that is Purified and the LP Groove has been as optimised for the Stylus as can be achieved. 

There is in certain Countries only a little cost required to be outlaid to create a Purified Vinyl LP, as the volume of substances required to produce the Cleaning Solution is able to purchased as a small volume.

This cost outlaid is negligible when there is the impression made when experiencing the end result, which is the perception that a Purification of the Sound is being produced, as well as the knowing not much better can be offered as a maintenance for the Source Medium and Stylus Interface within the Groove.