I really appreciate the feedback because I know how important it is to have synergy between the headphone, DAC, and amp. Does anyone feel that upgrading to the Chord Hugo TT is worthwhile from the Hugo or should I just look to buying the Utopia first? I feel like my money would be best spent on the Utopia as it would be the largest overall upgrade, but definitely want a desktop DAC in the future to complete my system and I want it to sound fantastic with the Utopia.
A good general principle is that it is better to invest in things
which do not get too quickly outdated and do not loose too quickly their financial value.
In the case of audio it is clear to me that speakers and headphones generaly
do not evolve as quickly as the electronic devices, do not lose value as quickly and are less prone to failure.
So I think that it is wiser to invest more in headphones than in the electronic gear.
In my case I already have invested quite much in a collection of expensive headphones and in-ears (see my signature, e.g. the Sonorous X and VIII, JH Layla, etc., are expensive),
and will go on with the Utopia,
but much less so in electronics e.g. my Pioneer U-05 DAC-amp is cheap and not TOTL,
then I bought a AK240 a year ago,
and just bought last spring my first headphone amp, the IFi iCAN Pro,
in the end it will be time that I buy a TOTL DAC, I am thinking of the DAVE, but certainly not before I buy the Utopia.
Wishing you peace of mind with your decision.