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I regret selling my Dan Wesson 6" .357: I got it for $175 at Warshal's in Downtown Seattle and after I fixed the sites that thing shot like a laser. Next most-regretted sale is a tie: my USPc .45 and the 5906 I ordered new are both missed, but a little less so now that I picked up another 5906.
 
I havent sold a LOT of them but....

I sold my first handgun I bought the day I turned 21. Taurus PT 92 with wood grips probably around age 30. A few years later I had two ATF agents show up at my house one morning wanting to know what happened to it. I sold it at a gunshow-no clue.

I still have my first .22 rifle from childhood.

Someday I will inherit my Great Grandfathers 1873 Winchester 32-20.

I do NOT miss the three handguns I traded for my Wifes engagement 1CT nice diamond. Colt Officers 1911, Glock 23 with a freaky cool SN & an old beater SW 357 I got from a pig farmer years ago.
 
I use to regret selling my CZ 75B!!! It was my first CZ (if I remember correctly is was made in 96) and for some reason I shot it extremely well. I sold it just prior to a family vacation and I needed to pay some cash for a bill.

Some how I lucked out: The guy I sold it to ended up selling it back to me! He had even made a couple improvements to the gun. I like my gun even better now and I will never sell it again... Thanks
 
I regret selling my STI Lawman. I sold it to fund my Dan Wesson Cbob in 10mm and wish I would never have done it. I'd get another but it's tough to find them without the ridiculous rollmark STI puts on them now. I swear their obsession with rollmarks is the biggest thing holding that company back.

My nice and clean, pre-rollmark Lawman.
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In college I bought a chinese mosin, had a chrome lined barrel, sporterized. I loved the thing. One of the most accurate rifles I have ever had. Bought it for $50, sold it for $75, so I could have gas money to get home. (Vermont to California). When I got home, found out that I really did not need to sell it, sigh.
 
Kimber Ultra Ten II It was the lightest smallest 1911 at the time that held 10+1 Sold it to a buddys dad in 2005. The guy is an older very smart collector. To this day he has still not shot it. I only put 100 rounds through it. Not very common pistol to find
 
Let me think for a moment,,,,NOPE! I must be one of the oddballs, I may have traded a couple,, but I've never sold one after purchase. I have given more than a few away to Kids, friends and family members that I would like to hold and shoot again but they all went to good homes.
 
It's a toss-up... I really miss my Model 10, but I have a 66 now. And 357 is of course better...
But I still wish I hadn't sold my Firestar M43.

No regrets on dumping the 40S&W side of the collection.
 
Back in '89 (or so) I bought a NIB Polytech AMK-762 from a dealer's ad in the Oregonian for $250.00 It had a blond fore & pistol grip, and the uber rare Galil-patterned side folding skeleton stock (without the ugly plastic square panels at the hinge area you see on most Chicom side-folders of that time.) My (ex)wife kept nagging me to sell it at the time, so I sold it to my brother-in-law for $500 (I owned it for about 4 years). I regret to this very day selling it... He still has it (thank gawd), but he won't part with it... the bastage!
 
A Winchester 1883 44/40 take-down octagon barreled rifle in 98 % condition, given to me by an old lady who didn't want her great grand kids messing with it. I shot up the box of ammo and couldn't find any more, so I sold it to buy a Langlitz leather jacket.
 

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