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I regret selling....

Super rare 1980 Tokai JB120 Jazz bass. Should never have sold it. It was beautiful.
I sold it to fund 1965 Jazz, but still ...

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...my vintage 1970s Dan Armstrong fretless lucite for about $650 about 10 years ago (value now $1500+?), a vintage Ross guitar compressor for $5-10 at a garage sale some 25 years ago (value now $600+?)...and I can't remember if I ever collected on the vintage Mosrite Ventures Guitar I took to Ray Henning's Heart of Music in Austin some 30 years ago (value $2500?).
How about you?...

I had that same bass (fretless Dan Armstrong) that I sold about 1981 for more than $1K, but I learned that it was quickly "flipped" to Tom Hamilton of Aerosmith for double what I sold it for.

What do I regret selling? -- There's too many basses and amps to list here, but probably at or near the top of my list (at least in recent years) are a pair of Muckelroy basses and a Mesa M9 Carbine amp.
 
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To be honest, I have no regrets. I've sold some very nice basses but it was because they weren't doing it for me. The one exception is my first bass, a shiny red Hagstrom HBII ($90 in 1971, and I overpaid). If I could get that one back, I would, but purely for nostalgia.
 
-1978 El Camino with a .030 over 1968 327, rebuilt with all-forged guts, 11:1, cam, heads, Edelbrock EFI, Tremec TKO 500 5-speed, 9", 3.70 gears and a Detroit Truetrac, all new suspension and chassis parts, all the goodies. Traded it for a nice 4WD truck when I got into my electrical apprenticeship because it was my only vehicle at the time and I needed something more long commute practical. I should've just bought a cheap FWD work car. I'll build another one like it one day.

-2000-ish German Warwick Thumb BO. My first active bass, I sold it because I didn't really know how to use it, being used to passive basses. That was about 2004-5, so before the days of ubiquitous limitless information, if Youtube had been what it is now or I'd known anything to speak of about the internet, I would've learned how to make it sound how I wanted. I'll buy another one someday soon.

-Didn't sell, but also didn't buy for the LUDICROUS price of 400 bucks, a 1946 Gibson LG-2 that I restored for a friend of mine. All I did was level/dress the frets, then made a new nut and saddle and had to clamp the neck into a bow for a while. He had inherited it, sold it for 700 (still ridiculous) but said I could have it for the work I did and 400. That thing was AMAZING, but I was saving up for a Martin 000, so I passed. I have two 000s now, a spruce and rosewood Stewmac kit that I built and a mid-2000s (I think) Martin 000-15M, and they're both SWEET, but I sure wish I had that old Gibson.

-My first really good rig. An Ampeg SVT 2-PRO in a rack with some other stuff (power conditioner, light, tuner, drawer, and an equalizer), 1-4X10 and 1-1X15 Hartke XL cabinets. Sold it all for less than a grand (I think 850) in like 2007 because I was broke and had other amps and was no longer playing big gnarly rock shows. I should've at least gotten what it was worth out of it, but I needed rid of it pretty quickly. Again, had I known about places like Reverb or here (if they existed then), I'd have been a hell of a lot better off.
 
I have probably bought and sold a music store full of instruments over the last fifty plus years but the only one that I really regret selling was a 1957 Gibson ES-175. If you don't know what an ES-175 is, it is an arch top hollow body jazz-box guitar with dual humbuckers.
I have never played anything over the years that sounded as good or played as well.
I bought it in 1964. It was new-old stock in a music store in California. Sat on the shelf for seven years.
That guitar was absolute magic. But I didn't know better. I was a dumb kid and let her go.
 
...my vintage 1970s Dan Armstrong fretless lucite for about $650 about 10 years ago (value now $1500+?), a vintage Ross guitar compressor for $5-10 at a garage sale some 25 years ago (value now $600+?)...and I can't remember if I ever collected on the vintage Mosrite Ventures Guitar I took to Ray Henning's Heart of Music in Austin some 30 years ago (value $2500?).
How about you?...
I don't have any regrets about selling any instruments.

On the other hand, I do regret selling some LPs when I was in college, and wish I had them back.