I took the deep dive into this hobby in the middle of the year, and fortunately have had mostly good experiences, but I can’t really narrow it down to just 1 purchase so I’ll divide it into categories.
Best:
Headphone: ZMF Aeolus
IEM: toss up between the TinHifi P1 and the Blon BL-03
Dac/Amp: Topping D50 + JDS Labs Atom
DAP: LG V20
Honorary mention: Thieaudio Phantom, Micca RB42
Been really enjoying myself and my music and all is good and right in my audio world. 
I think the blon 03, since I don’t have a variety of equipment I had never heard such a sound signature and the more I listened to it the more I love it!
Campfire Lyra II plus a Luminox Thunder MMCX 2.5mm upgrade cable, all for $2800 HKD which is roughly $360 USD, technically second-hand but the box was never opened and the seal was unbroken 
And thus began my descent down into the rabbit hole.
I bought a second hand AK Jr for $90 USD to compliment the Lyra II, those who have bought the M11, do you think it’s worth it and do you think it’ll make a big difference in terms of audio quality? I know there is a huge difference in the interface but I’m not sure if it’ll be worth the audio quality, even for second hand around $380 USD?
Edit: might as well add, the reason I got the Lyras at such a low price is because our local stores are trying to clear some of their less popular products, so they put out a $1800 USD bundle for an A&K SP1000M (Moss Green), Campfire Lyra II and the Luminox Thunder Cable. I would’ve purchased that if I had the money (I’m still studying in Uni and yes, I’m aware that this hobby will break my bank and leave me homeless in the future, but hey, at least I’ll have good music).
2019 has been my 1st year into this lovely hobby…
HD58X and ifi Nano BL was the purchase to suck me into this black hole… LoL!!
Then I went down the DIY road for speakers with the Overnight Sensations powered by a Micca OriGain and a Tone Board…
2020, I think some RB42’s and 1990’s are on the wish list…
Well, I got into the deep end of the hobby this year. Stuff that arrived early this year: Monoprice Liquid Spark and an E-mu Teak. Relatively recently I acquired a SMSL SP200, a Hifiman HE-560, and a Koss KPH30i. I’m probably going to pick up one more pair this year, I just haven’t decided what it will be…
I feel like this thread is just people realizing they have gone down the rabbit hole (or will next year) lol
My wallet cringed just seeing what I’ve bought this year.
Genelec 8351’s to rear channels.
I dont know where to put this but its a side note regarding my 2 purchases is in regards to film/media watching. If your headphone amp has anything to simulate stereo Crosstalk on speakers (Chord’s X-feed, Ifi Ican pro’s mechanical speaker simulation) and don’t really know what to use it for/dont like it for music, it widens the sound stage just enough on films with a stereo mix to make it sound more natural.
Yeah it’s an interesting effect but not something I leave on for ifi products, I think it is good for stuff like stereo beetles remasters where it makes it sound less left and right
For me, without a doubt my best purchase is my LCD-X. That (combined with SOnarwork’s EQ profile) has really done it for me.
Hmmm, do you like sonarworks or audeze reveal more
HD6xx, SU-8, and Atom.
I have HE4xx and SP200 on the way…so this may need to be updated.
I’d go with the GuideRay GR-i, followed closely by the Blon 03. If the Blon didn’t need some help with the tips and such it come in first for me. The KBEAR 06 is another close behind those two, but the original cable that came with mine was shot, so it dropped down on my list due to quality issues. Great sound though.
How do you think the guideray compares to the blon?
Yeah with films, you need the cross talk more than music because the sense of imaging/sound stage needs to feel more spacious for films
I can see that because of how movies are traditionally mixed and mastered for 2 channel
If we are to call this year something like a title what would we call it? I kinda wanna dub it the Chinese invasion cause Chifi really came through this year specifically.
Sound wise I find them comparable, not a ton of difference to me. So you have to consider the Blon has it’s issues with the tips & cables, and the nozzle length for some of us. Where the GuideRay has none of those, and has a very nice cable. The GuideRay is actually one of the most comfortable iems I’ve encountered out of the box, didn’t have to change anything on them. But the Blon is about half the price, so there is that too.
Edit - Just switched to the Blon after using the GuideRay all day. The Blon has a bit more clarity to them. That may be some what due to me being able to use foam tips on them, but not being able to find any for the GuideRay yet. I don’t know…
Topping DX3 pro, not because it was the best audio equipment I got this year, but it allowed me to properly utilize a set of 15+ year old Adcom power amp and speakers (EPOS ES11) my dad had kept in storage.
Otherwise I’d say Fiio Q5s & Argons, love watching movies with them.