Upgrade my CD player or futile effort?

Using my personal experience as a description to assist with the OP's inquiry.
I am new to using CD in my System, it has been a Source for a few years only, to be accurate since 2016/2017.
I am quite familiar with CD and have heard it as a source in many systems and have had a fair share of CD vs Vinyl Demonstrations.
Until my commencement of using CD as a Source, I was convinced that a Vinyl Chain as a Source was the only stimulus I required.

What changed was not such that an experience with CD was responsible for the change, but more motivated by how I was perceiving the use of CD in relation to it being a Second Source to the carefully created Vinyl Source. I was forming the view Cartridge Life could be extended if CD's of the same owned Albums was to be used to create an alternate listening experience with new hard media for already owned Albums that are Vinyl. 
My entrance into the use of CD was quite blunt, I put a CDP from a sons bedroom set up into my System and kicked of with my Sons CD's to get going.
Nothing special going on, but music was seemingly more convenient as I was not feeling the need to be adhered to the listening seat, I could crank up the Volume leave a few doors open and get on with a few tasks.

This evolved into a want to create the CDP experiences with better known music and hence the Journey began.

At a later period in 2017  a friend loaned me a Heavily Modified and much improved CDP and this was to show the used CDP to be very wanting.
I was impressed with the loaned CDP and began to carry out Vinyl vs CD replay comparisons, and the separation in SQ between the two sources was not too distant. It was definitely not in the same separation that was noticeable between the two CDP's.

Then came dilemma time, must return loaned CDP, must decide how to replace CDP ?  CDP or CDT > DAC was now the new thought process.
During this period I also went and had demonstrations form HiFI Dealers who presented streaming sources with a value of up to £6000 and one was in a System that retails at £100 000+, I felt the streaming system presentations was not impacting on myself, or making an impression I could attach myself to and want to pursue.

I did not use my well tried and test methods of getting out and trialling devices on a shortlist.
An opportunity came along to purchase a DAC, that was a early Prototype Production from a designer who has a range of DAC's.
I took the punt and purchased the DAC.
The DAC was first auditioned at another home on a system I am very familiar with and know the CDP qualities that are available within this system. Both myself and the system owner was quite impressed with how the DAC had created very noticeable and impressive changes to the CD replay in this system.

Cutting to the chase the DAC after a period of trials with CDP's and CDT's the DAC has now found a place where it has been coupled to a Perfect Wave Memory Player Transport for the past few years.
I don't see a need to make a change as I have heard the DAC in quite a few systems with other CD Drives.
I have not spent any energy pursuing any further changes, even though I have been through a selection of COAX Cables and feel I now have a ideal Cable in use.

As a comparison to the Vinyl Source, I have chose to a selection of these with HiFi minded friends in attendance. I feel confident to claim all assessments will evaluate that the outcome of these are a close run race. I have noted that  during a 'same Album' Vinyl vs CD comparison,            there are differences to be detected, but let one Album play on in CD for a short extended period and there will not be any want to return to the other Source, the listening experience is totally satisfying. 

For less than the outlay of a Cartridge that would be classed as quality Cartridge but not High End Spec', I have a CDT > DAC and a good selection of CD's to be replayed.  I don't have to concern myself too much about a loss of SQ, as there isn't much to be detected.
I can have music sit down in the listening chair sessions and be totally content, or heard all throughout the house levels of music, through not feeling the need of being in the Listening Room, just increasing the Volume and I am free to vacate as I do not feel the need to monitor the replay extensively. My discipline developed with Vinyl will not allow me to have this attitude towards a Vinyl Replay.

My hierarchy of music replays are Vinyl
( Too Long a relationship with the care of the Vinyl Media, the reverence of the Total Luxury Cartridge Purchases, and the pursuing of knowledge for extending my understanding of the critical mechanics and geometric interfaces are a underlying obsession) 
CD follows, but now with a conviction for the Source, Listening Freedom and a SQ that I did not foresee being produced.
(Thankfully the CD Media does not cause me an obsessional pursuit of furthering my knowledge)
'Amazon Alexa' an Ancillary used for convenience and gaining Speedy reminders of music I am depriving myself of listening to on the system, as well as reminding myself of forgotten past musical encounters, this is a wonderful device as a Low Tech streaming method with a SQ that has room for many improvements. 
(My most extended periods of hearing music being replayed over the past 18 Months is through Alexa, the total convenience is quite unavoidable it is seemingly always turning out tunes)
Serious attempts at streaming are not seeming to become a priority, but I am optimistic that a method will be discovered to get my interest going.   
       
     

Very recently I have listened to a Denafrips Ares that was newly imported so I will assume it is the Model II.
This was compared to a Linn DAC that had recently received one of the Companies offered upgrade treatments.
The CDT was a Wadia Model from a bygone era.
The Linn was also used with a Streamer Device as well
Both DAC’s were with components that had almost Zero usage time, and the Denafrips presented in the manner that was making it look like it was getting the upper hand in the SQ.

At this same DAC demonstration, I also received a demonstration of a New Imported Phasemation EA 350 Phonostage against a New Design All Valve Phonostage.
The TT was a SP10R with Glanz 12" Arm and a Miyajima Cartridge.

The Denafrips Ares when compared to the Linn DAC stood out for its delivery, especially knowing it was needing a extended use to allow it to really offer the truth of its capabilities.
I do recall saying that in my home a Streamer with the sort of SQ being heard would be quite welcome for a second system to be used by other family members. 

Both Phon’s were in my view able to deliver a much more impressive presentation, when compared to the DAC’s but each Phon’ is close to Five Times the Purchase Value of the Denafrips Ares.
From my own personal preference, I prefer a CDT > DAC that can deliver in a manner that conjures up the thoughts of it sounding Vinyl Like, but I am sure this can mean very different thing to each assessing the experience.

The Denafrips Ares during the Demonstration, in its rawest of usage time did not offer what I refer to as a Vinyl Like delivery,  the Ares and the Linn has the shared traits of a more commonly experienced CD presentation and SQ, the Clarity and Lucidity is quite noticeably present, I did suggest at the time the experience would be a great to return to when each device has had a few hundred hours of usage. 

To keep the events during the demonstration in context, the Denafrips was sold to a attendee of the demonstration a few days after the event and the seller of the Ares purchased a Denafrips Terminator, I will hopefully hear this later in the year.
The All Valve Phonostage was retained by the systems owner and purchased.