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Most of the guns I regretted buying wasn't because there was anything wrong with the gun itself, I just regretted it because I A.) didn't really need it, or B.) ended up wanting something else later on.
But a couple guns that I did regret buying because they ended up being junk was a Chiappa 1911-22. Flimsy plastic mags, made out of cheap pot metal. Can't find anyone to buy the darn thing. ( wish my town did those "buy-backs" ) Another one was a Phoenix Arms .22 that just so happened to be my first handgun acquisition. It was another cheapo but on a budget not too bad. I gave it away as an xmas gift. Then I bought a .22 rifle made in the Philippines made by Armscor. Not a bad little rifle, but I only bought it because it very loosely resembled an AR15/M16. Same basic shape but that's where the resemblance ended, lol. I took a bath on it when I traded it in.
I have bought mostly older Winchesters, lever guns and Model 70's, an LC Smith double, Model 12, Model 42, some classic .22 rimfires including Winchester 62 I think it is - the Browning designed pump with exposed hammer, FN made Brownings, Colt SAAs, a few original Lugers, a few Ruger rifles and revolvers - so I bought quality. And so - no, no regrets.
I bought a Model 29 4" 44 magnum once, I bought it used off of Gunbroker, this was in no way a reflection of Gunbroker, but not being able to put my hands on the weapon before burying it was a mistake. I knew the 44 had some surface pitting; what I did not know was that it also had a major timing issue, that would cause the revolver to lock up hard. I had to remove the cylinder on it just to get it moving again. This gun turned out to be a turkey, sold it to another dealer.
I still wanted a 44 magnum, a year or so later I found a really nice 4" 629 with recessed cylinder; so I got my 44 magnum, only this time there was no issues with it. I had to spend much more than I wanted for it, but I got exactly everything I really wanted out of that particular revolver.
More like the common item that it never fits perfectly to the task for what it was bought, so then you are after another one.
I love my USP, it is what I will take most of the time. But the catch with the USP is that it isn't concealable unless you are wearing a field jacket. So I went looking for something smaller and bought.....
.......a Kimber Ultra Carry. It's small, it's a .45, but it requires a lot of care and preparation for use. One isn't buying $15 1911 magazines but rather $45, practically the cost of a USP (or an M-14 during ban) mag. It has a tendency to stove top. It works if you know how to use it but it takes a lot.
Since the small gun question wasn't answered, I got a Sig P239 on the recommendation of my arms merchant. I don't have too much of an issue with it except....it's not a .45. Is that really a problem? Well, it may have been the pistol that started making me buy 9mm. Different needs, add another caliber to that needed to be on hand.
I had bought a few Taurus handguns many years back before I learned my lesson, as none of them I had or tried of other peoples were reliable or accurate, one 5 shot revolver shot an inch to the left at 10 feet from a bench rest position, how it could do that was beyond me. I never even look at a Taurus products since back then.
My Yugo SKS, sure it looked cool with the flip out bayonet, and the sites and hook ups for the grenade launcher, and the glow in the dark flip up sites. It got to the point where it looked like I was trying to kick start my gun just to cycle in the next round.
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