Wondering what equipment you have purchased but today may make a far different choice.
Speakers, personally, are the most difficult decision since they are not auditioned (in many cases) in your own environment.
Curious as to how many replies this thread gets.
It’s my impression that people don’t like to admit their equipment mistakes.
At one point I was enamored with the concept of a passive preamp and purchased one and used it for a while. Eventually I had to agree that my system sounded much better with an active preamp and it’s been under a bed for about 10 years.
Also, after my ex-wife cross examined me one year about what I would actually like as a Christmas present, she kindly commissioned a technician to build me a passive MC transformer prepreamp. I used this for many years, only replacing it this year with an active MC stage that is far more effective and dead silent.
So I am over my passive transformer based gear stage.
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BOSE Lifestyle products. Nothing more to say.
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My first pair of “proper” speakers were from a short lived brand called Ram. They sounded good in the wall of speakers in the shop but were set up to sound exciting so grew wearing at home.
I bought them in 1980, their good point was they were built like tanks and are still going strong at my sister’s house.
My linn sondek. My wife wouldn’t let me put it on a shelf and we have a bouncy floor… Didn’t lose money selling it. Went back to a technics sl-7 which is immune to kids and bouncy floors.
Beyerdynamic headphones, they sounded great but deemed it their life’s mission to crush my head. eBay.
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You should have used one of those stands with Pointy Feet , they make nice mess of wood floors , WAF = -10 
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For me, it has always been speakers. My current speakers were very well reviewed. They are not expensive, but they do not sound good in my listening area. My wife wants me to hang acoustic panels. Here’s an interesting side bar: I was “listening” while on the computer. Roon chose a Stan Getz album. It truly sounded very good. Sounded much better than other Qobuz selections (or CDs, SACDs, etc). I then look at the Roon interface. It was a mono album.
Aside from these speakers, I was not pleased with the Paradigm 100 v3 (now in my son’s apartment along with its subwoofer) and really displeased with Magnepan SMG from years ago.
I’ve gotten some pleasure out of almost everything I’ve bought. A few times something seemed like a good deal even though I had no immediate need for it, so I bought it, and then a year later it was still sitting there. But then voila! some need arises and I had that piece stockpiled!
My biggest wish is that cutting edge AV receivers and pre/pro’s would not go obsolete so quickly. I.e. that firmware updates were available to make them work with the latest formats and protocols. I know NAD has some of this with their upgradable cards, but that doesn’t look to be a lot less expensive than churning through new gear. So that’s why I’m at 5.1 and 1080P when many have Atmos and 4K.
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I’ve swapped around a fair amount of kit over the last year and am now at a point I am very happy. Much of what I bought though has been secondhand and consequently I have moved a lot of it on for very little loss.
Haven’t bought anything I have ended up regretting as such but knew exactly the sonic signature I was looking for so have played around with gear until I was happy.
Money being no object I would prefer a pair of Spendor D7’s instead of my Rega RX3’s but I got the 3’s at such a good price I just couldn’t justify the extra.
I had the top of the line Pioneer A/V…then the Onkyo…then the Yamaha…and now the Denon. Denon, at least for awhile, had firmware updates. I still think it is inferior in voice reproduction.
I believe we buy A/V receivers for a 3 year lifespan. Since we use ours only for movies/TV and only a few hours in the evening, I personally would not get so many channels. I use three outboard basic amps (Onkyo) with the Denon.
Stereo purchases, for us, has always been a long term commitment. I think the Jay’s Audio CD player and the Denafrips Terminator are long term (for us). I would not buy the redundant (for us) McIntosh MCT-500 solely for SACDs were I to do it over again.
Aha, if we can include AV equipment.then I deeply regret buying a surround processor and 5.1 amp from Outlaw Audio. Neither have ever worked completely.
I now use an Onkyo for the surround channels with HT bypass on my PL pre-amp for the front and an Outlaw monoblock for the center.
We had a 12’ projector and 14.2 channels. We bought an OLED for casually watching TV. Then found ourselves never using the projector and watching dramas rather than action movies, did not use the surround channels. Donated the projector and screen, use only the OLED.
Back to stereo, when I was in school, hi-fi purchases were very serious since I had to justify to myself that I would spend funds that I did not have. Each purchase was emotionally critical. Today, not so much. I am, however, a Roon and Qobuz fan boy although I likely use just basic functions of each. Wife loves all music and likely considers me her DJ.
Great planning and wonderful outcome.
We have very few places at which to audition equipment ranging from mid-fi to very high end. Was not helpful in our case since our room (s) are quite different from the audio (and most often video) showrooms.
My wife likes to watch/listen to music videos (DVDs and YouTube), especially that which comes from my generation (especially Blues). So we are still seeking improved audio.
I bought a Linn DS/3.
I already run a Chord M Scaler/TT2. I wish I’d bought a Chord DAVE instead of the Linn DS… 
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I wonder “what are the true costs of undoing a decision.” Equipment depreciates. It is much like staying in a subaverage relationship or riding a job until retirement despite burn-out. But rather than mildly lamenting a decision, it may behoove us to consider bailing and buying the other unit.
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In my early stereo days, I bought an expensive (to me) stereo receiver, but since separates were “clearly superior,” I bought an even more expensive pre-amp, amp and tuner. “Sadly” the tuner was tube. As soon as the company released a solid state tuner, I traded for it. They also began to phase out their tube pre-amps and amps, and I followed them (down the rabbit hole). Today their tube equipment is treasured. Their solid state…not so much.
I soon realized one reason for working hard is not to have to worry about poor purchase decisions; merely move on and try other equipment.
My wife said when I lamented not having bought a `59 Les Paul “it would not have mattered…you would have traded for a 1960…”
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For me a Perpetual Technologies P3A around the year 2000. It was an early example of a sort of outboard digital filter processor that was paired with the P1A DAC. Highly thought of in its day. The DAC was great. I used it for years, but I could never hear a difference with the P3A. Drove me nuts, fooling around with cables. Madness. Never heard a difference but I just never gave up trying. Still have them. Getting an itch with the lockdown to get them out again. The DAC, no regrets but the P3A I really wish I had never bought it.
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For some of our purchases, they do give us a lot of time for experimentation and exploration. I think that may be our take away.
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There is a YouTube Channel, perhaps you know it, where this fellow modifies speakers (such as ELAC etc) and builds his own. He refers to the gap between production costs and sales price. He also indicates that he has ever evolving speakers of his own. Again, I do not recall the name of the speakers.
Home theater. It seemed like a great thing for about 5 years, but now I wish I had spent more money on the stereo/music side of things. I ended up with two systems, one for home theater and one for stereo, and I rarely use the home theater stuff.