How to get into high end digital? (Feeding a DAC)

JasonBourne says..‘The same thing applies to cables. Cheap here works just as well as expensive. A $10 Monoprice digital cable is indistinguishable from a three or four figure cable - regardless of what the "golden ears" crowd claims.’

LoL! Way to go to get things off to a contentious start! By the way I enjoy your posts and respect your opinion greatly.  On these two areas I would have to offer an alternative opinion though.

A) Digital Transport (for CD) - the Oppo UDP-205, Pioneer BDP-09fd, and Parasound Halo D3 all sound different. Even if the DAC is supposedly indifferent being asynchronous, As far as signal from CD transport, it is not all the same sound. 
B) Digital cables sound very different. The Black Cat SilverStar MkII I received from CFarrow is ultra high res. And provides a super-clear window on the music. The Black Cat Veloce is very good, but not as good as the SilverStar. Less resolving. The Canare is well behind both.

Cheers!

Digital is a very deep and winding rabbit hole but a potentially fun journey.  Long and short of it everything matters which means there's lots of avenues for improvement after you start.

First buy used for best value and return when upgrading.  Get a good DAC, add a reclocker like an IsoRegen, some decent USB cables like Curious, some decent digital power cords like Wywire, some powerline noise reducer like PS Noise Harvesters, then a real music server- start simple line Bluenode and upgrade later and enjoy.

I much preferred my Wyred4Sound DAC over my Yggy,
see: https://wyred4sound.com/products/clearance/dac-2v2se-trade-units
it includes a good volume control.  A lot is made about R2R but the W4S was just better sounding all around.  I traded up to a Denafrips Terminator then TP.  I would recommend anything Denafrips but the used market is small.

Check out US Audiomart and https://audiophilestyle.com/forums/forum/18-buy-sell-audio-and-computer-components/ for used digital gear.

Forget all that stuff. Pitch it all out and get a set of the Dutch & Dutch 8c.   Not only are these loudspeakers amplified, they have built-in DAC and DSP EQ. All you need are them and a digital source like a laptop, an iPad or even just your cell phone with Roon.

This sounds like the question I either asked, or was thinking… which was, “What about a Lyngdorf TDAI 1120 ?”.

The Dutch-n-Dutch sounds even easier.

I suppose it would be appreopriateto ask if we should go halves?  ;)

Wireworld makes nice fiber optic cables made from glass. 

Well We’ve been to the Corning museum in 2018. Whether is It glass or plastic, the physics is the same over the short haul. I am skeptical that one can “hear” glass as being more transparent.

JasonBourne says..‘The same thing applies to cables. Cheap here works just as well as expensive. A $10 Monoprice digital cable is indistinguishable from a three or four figure <digit (sic)> cable - regardless of what the "golden ears" crowd claims.’

Well 3 or 4 digits is most of the way to a fist, which seemed like it was his point.

And I doubt that the manufactures are not using 2000 $/foot cables inside of their gear.

Fiber optic provides complete isolation from the noise in the power supply of the sending unit.  Coax does not.  Galvanic and isolation transformers still pass noise through the ground. 

Ok so we are not talking about digit noise as in the bits are getting bit error rates > 0, but traditional analogue circuit noise being passed left to right through the signal chain?
(If so, I think I get it now… thanks!)

I must beg to disagree with any reclocking naysayers.

When there is a measurable difference in dither, then I would have to agree with you. If the particular device has a clock that is as stabile or more stabile than the reclocker, then that make the reclocking appear to not work… or not be needed. So asynchronous (file based), with a buffers, would seem to remove a lot of that need?

Go for Roon.  Use one of Sonore Optical solutions and all your noise worries are gone. Get a USB capable DAC. Most are now. Feed that from just about any digital library. No discs needed. Rip them all to even just a usb hard frisbee attached to the Roon server. This solution can run from 6500 for Nucleus + Signature SE down to 2000 or so for Sonore cheapest solution with had built server.  You will not be disappointed. 
I have had a few DACs and moved up to the signature se and ps audio Directstream.   Wow. Enjoying some Ken Mo right now. It’s so clean 

A set up like the one outlined below in the second bottom paragraph should fit in correctly with the Title of the Thread and the OP's inquiry.

From descriptions offered to myself following inquiries, it is certainly  going to be a very different experience and will fit in the OP's requirement,
 "But high-end to me would be something that sounds good and does not sound like it is obviously coming from a CD player."    

"Well I was not thinking much of budget, but less than 10k."
I think a prudent approach can get you to this level of set up with quite a few $$$$'s left in the coffers, leaving enough for a HQ Player Subscription for many years if this method of replay is investigated and becomes a High Up the List choice.
 
I have followed various user experiences around this method of replay during the Lockdown of 2020 and after a long hankering to experience the set up, it is looking most likely I will be able to have a demonstration of the set up later in 2021. 
I am taking a friend along who is a very adept EE and Digital Enthusiast to the demonstration, I am hoping the EE develops a curiosity for this method and carries out a build, this will make it much more accessible for myself to experience, as at present the Trip will be between 300 - 500 Miles round Trip depending on the venue.

A DSD decoder set-up as a source with a 'Valve DAC'. used 
with HQ Player upsampling to DSD from PCM FLAC files and DSD256 Tracks.

A Thread covers this arrangement and other very similar set ups on the DIY Audio Forum