This upgrading urge can prove to be expensive and frustrating – been there, experiencing that. But I sense that a lot of the time thae urge comes from familiarity breeding contempt When one hears or reads about another good system B, that comes across as different, it can appear more attractive. However, it is most likely really no better overall than the present system A . However the mind concentrates on something like e.g. the soundstage which does seem to be better with B but overlook other aspects of the sound which may actually be slightly worse than A.
So, could the answer be to have two different systems rather than be continually “upgrading”? With the latest relatively inexpensive quality Chi-fi now available this suggestion is not as crazy as it sounds .Topping and other companies offer a range of options with different sound signatures, even within the same brand. One amp/DAC combo could be chosen for resolution while a second system could be chosen to sound more “musical” (exactly what that is very subjective and will vary widely). A further approach could be to also have two different headphones and that would give more mix and match options. Confronted with two different systems A & B, it would soon emerge that A suited one genre of music better while B reproduced other types of music better, What fun!!!
And yes, I’m currently in that situation now and sometimes prefer the Topping DX7PRO+ to the Audio-gd combo of Master 9 headamp & R8 DAC. They sound different but music is enjoyable on either with preferences sometimes depending on the music being played. This might appear incomprehensible to some but it does underline that e.g. a good relatively inexpensive system like the Topping can compete with much more expensive hi-end items like those from Audio-gd - the law of diminishing returns is alive and well.
This inane suggestion of two systems is unattractive for speaker setups mainly because changing from A to B is not so easy plus the speakers and room resonances most likely overpower the observed sound anyway.
But to finish up, here is a crazy bit of irony. I’m considering “upgrading” the Topping DX7 with a DX9. So having multiple systems really is not working for me - I’m still obviously still suffering although having a lot of fun. But if you have stronger will than me, it might help!
My headphone setup is simple and I stopped thinking about upgrades the last few years.
Roon on MacBook M1 → Cambridge CXN v2 as dac/streamer .
XLR out to Singxer SA1 Headphone amp.
Turntable RCA into waxwing phono stage → coax out into CXN V2 and from there XLR obviously in the Singxer but also spdif out into my stereo system .
I also have the option to either go coax out from the CXN v2 to another headphone setup or spdif out from the waxwing to something else.
The CXN v2 also Supports AirPlay for my Apple TV 4K and usb in for my MacBook .
It’s also a fully transparent great dac with 384khz upsampling.
I also got a SMSL SP400 and D300 that I occasionally switch into rotation (coax out from the CXN v2)
Having multiple good options and way to connect and switch out equipment is important to me in case of hardware failure and to troubleshoot software and hardware issues
Headphones are meze liric and Dan Clark aeon noire
According to my experience this situation quite often evolves from particular tracks sounding astonishing on this system B so if you listen to it at a friends place or dealership or trade fair you get this ´Oh sh… it sounds better than what I have at home, so I need to upgrade´ just based on a very limited number of tracks.
In many cases it is easy to ground oneself by trying completely different types of recordings on that one which you would want to sound good as well and for which you love your system A. The broader the spectrum of recordings the more likely to reveal flaws and shortcomings of that new system.
Do not see the point in this unless you have very specific ideals of how a system should sound with this or that recording which are absolutely impossible to achieve with just one system.
For example if you want at times to have the maximum of dynamics, gripping impulse response, direct and ´live-rock-like´ sound with certain recordings and maximum of silkiness, depth, ambience and relaxing transparency - well, it might be impossible to achieve both with one system.
For everything else, I would rather try to set up one system achieving the maximum of your aims.
Of course there are amps and DACs sounding smoother or more dynamic or offering more resolution than others in a direct comparison. But I have never experienced differences in components so overly huge that I would need both options. Huge differences as well as an unchangeable ´signature sound´ is rather a matter of choosing the right loudspeakers or headphones, not so much amplifiers or DAC.
So I would rather go for having several pairs of headphones than several DACs.
I spend about half the month at home listening with my Pioneer HPM 60 speakers. Then, I spend the other half month at my 101 year old MIL’s listening with my Focal Clear headphones. This switching back and forth seems to keep everything fresh and sounding good. No urge to upgrade either, although I am starting to get an itch for a Roon Nucleus Titan.
Don’t confuse listening to music and searching for gear. Many people do it simultaneously. That is a mistake. If you really get bored by your system take a break and revisit it after two weeks. This will cure most itches. Also I think 99% of all new products are redundant and bring nothing new. New products rarely bring something really new to the table. Buying second hand may bring you great deals. My 2ct.
I have two headphone options in my listening room, one open (Senn/Drop HD 6XX) and one closed (DCA/Drop Aeon X). The HD6XX work great right out of the headphone jack on my Yamaha AVR, and I have a little xDuoo tube hybrid amp with enough juice for the Aeons.
The closed were bought primarily for when I need a touch of isolation, but I love them so sometimes I’ll grab 'em even if there isn’t that need. So that helps keep from getting “bored” with either one, and of course I have speakers for when that’s my preference.