The one guitar you regret most parting with?

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1963 Gibson SG Custom. Sold it to a friend for $200 , with original case back in 1981 when I was a starving college student. Now, the loaded pick guard is probably worth $3500. He didn’t pay me for over a year.
 
Yeah, as starving student: sold a 68 pink paisley tele for 500 ,- around 85, 87... ****.... 15 years ago i purchased a new one. White. Standard. To have the tele twang back.... Aaaargh..
 
Only semi regret..
I sold it because it was not very loud and I lost half my hearing in my right ear.
I used the money to buy a Martin D28A 1941 Madagascar Authentic and a Baker Stately Homes Walnut Kneehole Desk that I loved that was discontinued just when I was going to order one in 1992.
It was a J200N Natural Prototype A the first Bozeman Montana Guitar made by Ren Ferguson and assistant in the summer of the year before factory opened. It was shown at NAMM it was dated 1/15/1989.There were three Prototypes A .B..C. This was the Natural one.The bridge and fingerboard looked like Brazilian .The guitar sounded after it broke in after 10 years like maple syrup as my wife put it.Not loud but probably the best sound of an acoustic Ive owned..
The acoustics I have are all loud (2 Lowdens, Huss and Dalton Braz. and Authentic D28A) but I'd rather play electrics anyway.
 
I am not really a buy and sell guy..I buy intending to keep. Everything has a reason to have been sold. A 1989 Prototype (A) J200 made in 1988 by Ren Ferguson and an assistant in the summer before the factory was built that was shown at NAMM January 1989.That was regretful, cause it developed a sound like maple syrup.As far as sound quality it was probably the nicest acoustic sound..but the guitar was not loud with standard bracing and my right ear had developed partial hearing loss so I sold it.
A semi regret is selling my Les Paul Standard Historic 59' (1993) It was the first one made. That was a special guitar. When it arrived on 48thSt it was freaking expensive and the talk over there but my brother was down there every day and I got it.
I sold it to have more of a down payment for our first house a year or two later. My brother in law has it, I love the guy so Id rather he has it than I have it.I also had one of the first 1959 Reissues made as well in 1984 by Norlin.
The first 12 came to 48th Street (Manny's) all except two were bought instantly to go to Japan. I got #0011.
They were numbered 0001 to 0012 ..I don't remember if there was a 9 with space before the number.That guitar was caked in polyurethane.. it looked and felt great but never really developed magic..so I sold it.
 
Yamaha SG 2000. Great guitar. Red. Was my primary for a few years. I miss her. If I wanted to beat myself up over a foolish sale, no doubt it was selling a '70s Gibson Flying V (back then) so I could buy a suit to attend a function with a girl who I was crazier about than she deserved. Wore the suit a few times, she's long gone, and so is the guitar. Man, young love is stupid.
 
White EJ Strat. Neck was a little sticky but otherwise it was fabulous. Paired nicely with a Lone Star Special.
 
Wish I had this PRS Santana MD back:

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I had a Sunburst '88 Strat Plus that I put a tortoise shell pick guard on. I was broke and a single Dad, sooo.....
 
I just realized the link I placed is no longer available. I did not have many color images of the Gibson Les Paul Spotlight Special, most were in black and white. This was back in 1984 and did not have any color film except in the polaroid camera. Sold it in 1999 due to a divorce. Nice guitar but heavy. I got what I paid for it in 1984 (under $1k). Found it on reverb, sold for $8000+. It is not the fact I lost out on an investment that I have regrets. It was that I had to sell a favorite guitar.
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