I would like to hear from anyone and everyone about why each piece of your gear in your collection stays in your collection instead of being sold off.
so would my wallet
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Tbh I hate dealing with people while selling gear and unless I really need money it is not worthy me getting anxious about that.
Plus to certain extent each item is point on my journey. Will sell or give away some thing in the future cause I don’t want to be hoarder
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Well, different amps and dacs sound different when paired and can make some headphones sound very different and much more enjoyment. As for headphones well they have their different sound signatures. Something like a T50rp from fostex is super moddable but despite it being a planar I know others who keep the Sundaras as well due to just how much more open and detailed they are. I keep the dt 1990 as well as the T1 as despite being similar I find their uses different. T1 to me is very laid back it’s not the analytical headphone and it’s brighter to my ears meanwhile 1990 is more towards a neutral kind of frequency depending on the pads it’s frequency changes quite a bit when you pad swap it making it quite a special headphone in my collection. Nighthawk carbons, well there just hasn’t been another headphone like this one that I have auditioned… while it got kind of close when I auditioned the audeze lcd-2 it just wasn’t as good so I kept this as a special part of my collection.
Of course there are headphones that take the place of others in my collection and eventually I will sell them off if I feel they truly are essentialy in the same usage for sound just better to me. Each item is part of the journey and I find so much enjoyment in my setup switching off between the amps and headphones I sometimes find surprises even in certain songs that while I didn’t find very enjoyable at first suddenly they are very enjoyable with particular headphones and their amp and dac setups. I tend to keep certain headphones for particular genres of music. I wouldn’t pick up a Sundara for a very bass heavy metal band for instance since it doesn’t have a whole lot of bass instead something like Tygr 300r or Argons are great for this.
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Some of the stuff I find I hold onto I find the equipment I have tested with just don’t bring out the best in them. My K550? The one that was my step into HiFi? The BasX A-100 is the best thing I have to pair with them. The warmth is just soo good 
Other items, like my BL-03, I don’t care much for the fact that it feels like they are missing out on low end (same as the M220 Pro I gave away) but I could see being used for testing for the frequencies they tend to hit better.
Further still, some other items (usually IEMs again) I’ll keep on hand to let people borrow. Or I will keep on hand to show people what the difference between their Skullcandys/Beats and something actually worth their hard earned money.
I hope you don’t mean individually or there are about to be some really long posts lol. I keep the headphones I have because they are all different and I don’t believe in a perfect headphone. I’m sure I own headphones that others hate and even headphones that I hate at times but I keep them because of those “magic” moments when the headphone stumbles across the perfect song for it and presents it in a way no other headphone can. I assume it would be especially true for one that is made to be pleasing with everything. I also really enjoy the different ways a single song can be experienced just by changing headphones.
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Only if the writer wants to spend the time to write about each individual piece. The more detailed a response, the better of a read for me.
I learned years ago in photography not to sell unless I absolutely have to. There are cameras I wish I still had despite having sold them for “better” performers. So I have every headphone I’ve ever bought. A Beats Solo HD and an M50S are both held together with gopher tape. They serve to remind me what I was listening to back when, while also providing fodder for testing EQ strategies.
A fire sale Senn HD 579 I bought as a test case to see whether I could get away using open back in my household environment has a hideous native tuning. It sat idle for two years, except for EQ experiments. Then just last week I applied what I’ve learned recently on the EQ front. To my amazement they’re now quite an appealing change of pace from my DT 1990 and HD 600. For another person it might have been a new amp or dac purchase that bought them to life, rather than a new EQ approach.
But I’ve lived on a shoe string budget too. If you have to sell to upgrade, then you do. Just pray you don’t regret one or two of them when you’re older and wiser, grin.
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I have done a LOT of buying and selling the last few years. I am at the point now where I am pretty damn happy and content. Certainly with DAP’s, amps and probably DAC’s.
Having said that, I am almost never not thinking about getting more 'phones. I am currently almost pushing the button on two very different headphones and I have to call a guy tomorrow about some possible opportunities.
I also HATE selling stuff so I might just start hoarding stuff. I have been trying to sell two amps for a month and am tired of listening to stupid shit from people.
I am currently unemployed so I spend WAY too much time on this forum, Head-Fi, Drop, CAM, etc.
Oh yeah right, the reasons for my collection: I love music and got hooked on the variety of sounds, although most of it was almost special.
In the last year my gear has gotten SO much better, that I am now more hooked than ever. 
I really do not to sell some items… reduce the count and improve the quality. I have a hard time letting go of things I like.
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I would have a hard time deciding what to get rid of. I try and get headphones / IEMs / equipment that sounds different to what I already have. That way I have something for every purpose or whatever mood I’m in.
In the future I might give away any similar items I have as gifts to friends if I know they will be used and not just left in a pile somewhere.
So if something sounds great to me and can also offer variety in the collection, it can of course stay and separate me reluctantly.
Then I also use the stuff until it breaks.
I bought a lot in the last year and gave it back because it was great at first but got bored quickly.
Or didn’t like that it was worth keeping.
They weren’t bad, they also picked me up emotionally, but unfortunately not in the long run.
That’s why a lot is going on again.
I would not like to mention about products themselves that would be unfair because everyone should get an idea of it and then you can exchange ideas. Of course there are also things where you have made by reading here in this forum and very good help where you can find it It is proud to have made it, like the famous Fostex Mod for headphones, something like that always stays in a collection, of course 