My experience is that regretting a sale and buying something back ends up reminding me why I got rid of it in the first place. I stopped doing that for this reason. But if you sold for financial reasons, then it’s different off course.
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Virus TI around a decade ago. I sold it because I was so frustrated with the TI aspect not working properly despite trying everything I could, including several USB port cards etc… I tried to forget about it but ended up buying another and it stays for good now unless I’m financially forced to sell it. I use it as hardware only these days, although the TI does actually work great with my current PC.
I’m actually on my 3rd, I lent it to a mate who fell in love with it, so swapped it for his wavestate and bought another.
Other than that I generally find it pretty easy to move on from gear I’ve sold, but I have got to a point where I like everything I’ve got a lot.
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Intellijel Atlantis
I sold it and bought it back a few years later. its the only time I’ve ever felt regret selling a piece of kit.
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Gear I absolutely regretted selling within hours
Yamaha CS6r
Yamaha AN200
Yamaha DX200
Novation Nova XXL KB
Emu Orbit 3
I haven’t sold anything been thinking about selling for years but fear of regret puts a brake on it.
I’m the opposite, if something sits unused for a long time, it goes (aside from one or two sentimental pieces). There is a fairly active used market here in Japan though, so I know I can pretty much get anything again if I wanted to (aside from a handful of rare items I’ve owned). In nearly two decades of this, I’ve only come to miss a couple of things. Sometimes I think it’s good to let things go.
I regret buying way more often. 
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I’ve got a few things I could let go that I regretted buying, I.e vp-03 but don’t think anyone would want it haha.
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Not happened yet, but might be an imminent regret in the making:
I am thinking about getting rid of my Moog Matriarch and audio interface and just go A4 + some Chase Bliss pedals. Yes, would be instant regret. Does it stop me from considering it? No.
I might even get a Sub25 next to it to still have half the paraphony of the Matriarch while enjoying the A4… For the same price mind you. Well. We’ll see.
If you want to go that route, one thing to consider might be having a Grandmother as a sort of Matriarch substitute. (Haven’t tried that myself, I also have a Matriarch.)
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I had that originally before replacing it with Matriarch. I was missing the paraphony a lot. Plus with GM patching never felt like it made sense to me sonically, good mostly for acid ugly stuff. There Matriarch is better, being focused a lot on stereo modulation.
However that spring reverb… Never heard anything better.
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MD sps1 Mk1
Mc202
Fender deluxe reverb 1968
Complete selection of minifooger moog guitar pedals (
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Pain.
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I still hear the delay in my sleep…
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I can only imagine. 
Managed to get the md and mc202 back but not the others
Corrected.
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Oh boy…let me think off the top of my head I’d say:
Monomachine
Moog prodigy
Juno 106
SH-101 (In red)
Nord lead 3
OP-1
Bass station 2
MS-20mini
Blofeld
An1X
Korg ms2000b
Microkorg
Moog theremin etherwave
Korg Polysix
Yea I used to have a serious problem buying and selling gear, Especially in the early/mid2000s when synths (vintage ones in particular) were a lot more affordable. I used to buy a synth, learn it inside and out, push it as far as it would go then get lured away by the next new shiny thing that caught my attention. There’s a lot of synths I’ve sold that I don’t regret at all and the gear I replaced it with I like better/works better for me but man for a while I was selling and buying synths every few months. I broke the habit within the last decade or so and I don’t sell anything ever unless I can absolutely justify it ie I don’t use it anymore or don’t like it or in some instances it becomes worth more second hand than it’s worth to me. That was the case with pretty much all the vintage synths I’ve owned, I would never pay more than maybe $600 for and SH101 or Moog Prodigy or more than $800 for a 106 or Polysix because in terms of sound and functionality they frankly aren’t worth more than that. Having said that I do miss them because they were great sounding and fun synths but when a Juno I bought for $400 all of a sudden becomes worth $1500+ it becomes difficult to justify keeping it when I can get put it towards gear that takes me much further.
All that being said I would love to own all the stuff I mentioned again but unless I become ridiculously rich somehow I’m sure I won’t ever buy them again (with maybe one or two exceptions like the NL3 or OP1 as long as their prices stay semi-reasonable).
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my one regret 
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I avoid sellers regret by keeping everything even if I haven’t used it in a decade 
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spoken like the smartest man to ever live.
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