For personal, sonic, aesthetic, investment reasons?
my NAD c350 amplifier. It is the first amp I ever got, I still use it even though it is in it’s last legs. Sound keeps getting muffled on the left side so it’s either so old isn needs to be recapped or it is just dying 
. I’ll never sell it, it isn’t worth much, but I’ll probably have to get rid of it soon
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Great topic!
My motto is never say never. 
BUT the audio item I would be LEAST likely to sell is my beloved Massdrop x Focal Elex headphones. Damn, I love those cans.
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I don’t have too many in my reincarnated audiophile stage but My iFi Micro iDSD (even if I get a Hugo2) and my P1’s love that pairing 
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My Massdrop x Empire Ears Zeus, I’ve tried a lot of headphones and IEMs and these are easily my favorite, they fit my preferred sound signature perfect and I sold my first pair and regretted it so i’ve learned my lesson. Got a great deal on them as well so that helps too.
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even if I upgrade I dont see myself selling the liquid spark its just sucha special piece of gear.
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My chord hugo tt2
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Upscaler?.. 
just jealous lol
My Fearless S8F iems… Perfect for me.
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It’s hard to answer that, because I just sold items I thought I would never sell. I think the items I heavily modded or tinkered with I have already made the decision to keep.
Everything else, I’ll probably cycle through eventually. I’m more likely to resell an amp or DAC than a headphone though.
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I haven’t gotten the upscaler yet (pandemic) but plan to if this script of the show I write for sells
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I would too…Hugo 2 first for me…slow.slow catchy monkey 
My Harbeths and my Nighthawks
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At the moment my Nighthawks and my old 558’s Great memories with those.
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i do not have anything else that can not be replaced. i do love my amps i have atm and can’t see me selling them ever, but you never know.
the power and noise filter i will keep until it no longer works because there is no usb2.0/3.0 lol. makes noise motherboard’s silent and eliminates most ground issues. its tiny and can be taken anywhere for any usb source. while not universally helpful, the last thing you want, regardless of where you are at, is extra noise.
Yamaha as-2100 is the first amp I purchased after a slew of used gear and I’ve only recently been able to really appreciate it… one day it’ll get the speakers it deserves lol
Also hd650’s being the first headphones that really thoroughly impressed me and continues to improve with gear so I’ll buy it more high end tube amps and keep it a long while
Edit: and nighthawks because unique
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Elex all rounder, near perfection. Aiva’s love the close soundstage and detail. Arya, big drivers!
KSC75. use them all the time. I sometimes look at them and say for the 100th time “amazing what they can do with technology these days” Cant sell them anyways. how much would i get? 7$?
Might sell my Auteur. I like it a lot. Great timbre and nice close soundstage. Neutrality kings. Its a little warm and can get congested. cough drops dont work. Maybe i’m crazy but i think i can do better.
Ebony. the best closed back i got. Great sound, wonderful bass. Sometimes i listen to them and i think “My god, these are the best cans i have 
” But leaks sound. Treble a little too harsh. and the Fostex th900 are calling. again maybe im crazy to do this.
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My record & FLAC collection… The gear can always be sold and relatively easy to replace. I spent many hours scouring the music sources that I want to listen to (physical). I don’t stream.
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i will sell anything if i find better.
Won’t sell the brand that i like.
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My 5 meter headphone extension cable is a keeper. Other people have wireless headphones, I have a combined 8 meters of freedom when I desire.
Another keeper is my collection of adapters. I can adapt almost any analog connector to any other with no more than three adapters 
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