As ever in hifi its always about marginal gains, as it is with everything we buy! 2 cars travelling at 100mph is 100mph, it's the experience of getting there. Fit and finish, hand built vs machine built and so on.
It boils down to simple economics if they made topping's in the exact quantities, using the same materials and labour that Chord implement, toppings would cost the same, but topping make millions of them with little human intervention so you reap the benefits of that and the pitfalls that come with such massed produced products.
To answer your question of "how much to better?" To truly better a product (not just subtle changes) yes you are probably looking to spend north of 2-3k to truly get your "pointing a Rick Dalton" moment
My experience for what its worth:
I can't hear much of a difference between my Dac and NAD c540 over a short listen but as you listen closer those differences become more apparent. And quick AB's can be done with the amps line selections. Now they aren't night and day but they are very much there and there is a presentation difference. How much value you place on that is up to the individual, Do i regret my choice? no. Would i do it again? yes, because those changes to me are beneficial.
I will say this, a CD player is built from the ground up and tuned with all it components in mind there's more going on than just a DAC chip in fact one could argue you need to pay more attention to the output stage and the quality of the analogue circuit, they should have been able to tune out any flaws within a CD player design.