I've regretted to some degree every gun I've ever sold except one (my Ruger 10/22 rifle, just never could warm up to it).
-Taurus 82. My first gun and a good one. I love revolvers and I love Taurus. However, it was a .38, I wanted a .357mag, I bought a .357mag and at that time I didn't think I'd own very many guns so I sold it. Stupid, stupid, stupid:banghead: .
-Ruger KP89. It was my first auto. I kind of liked it but I wasn't very accurate with it (no one that shot it was), I was much better with my buddy's Ruger P90. It also was too big and felt quite "clunky". It was 100% reliable. I sold it and probably shouldn't have since it was my first auto. I wouldn't mind having it back, or one like it, but I don't like the design enough to be very motivated to spend the money. I regret it a bit (a lot at the time) but that is tempered by the fact that I wouldn't have bought my Charles Daly 1911 without this trade and I like the Daly more than I miss the Ruger.
-Mossberg 500 Persuader- 12ga. My first shotgun. I loved the thing, when I bought it and first shot it I still remember the rush, the smile it brought to me and the feeling that "why did I wait so long for a shotgun". However, financial difficulties ensued and I figured that it would be the easiest to replace (not too expensive) and would give me the best ratio of used price v. what I paid for it of all my guns. Well, I still haven't replaced it because I can't bring myself to paying almost $100 more than I got for it to get the same thing plus I am somewhat limited in where I can shoot a defensive shotgun in this area.
-Taurus 605. Didn't like shooting .357 out of this little J-frame type gun, heavier than the 85 (.38spl) so seemed a waste to only use it for .38s and I needed money. I pawned it, planning to redeem it after I got my paycheck (I had just started a job and bills were coming due before my first paycheck would come) and then decide if I would sell it or just keep it as a compromise (occasional .357 at the range to remind myself what it felt like out of this gun and the ability to safely use any .38+P that came my way). Well, my paycheck was delayed and when it came I decided to let it go (I decided to sell) and I didn't want to rush to the bank and then the pawnshop to redeem it (I also figured the loss v. what I'd sell myself wouldn't be that great when adding the "interest"/extortion fee back in). Looking back I should have kept it- 1)I didn't get another snub for about a year, 2)it was a good gun, 3)I might have gotten used to .357 out of it, and 4)it could have been used with any +P that came my way or I managed to cook up (I now reload for revolvers).
-CZ 40B. It didn't quite do it for me. Not a great fan of the caliber, it was alloy so a little light for just a target gun and it was quite wide to be my future CCW for when I finally got to a CCW state (which was its intended role). However, it was reasonably accurate (more than "good enough", just a tad disappointing in light of my CZ 75B's incredible accuracy), it felt good in my hand (though not as good as my 75B), and it was a CZ (I love CZs). I needed the money and it helped me finance another gun so I guess it was fine to rid myself of a gun that I sort of liked but that didn't quite do it for me and that I rarely brought to the range. However, had I waited a bit longer and Walmart and Winchester brought out the White Box 100 rd value packs in .40s&w while I still had it I probably wouldn't have sold it.
That is it so far. The only one I truly "kick" myself over is the Taurus 82, but I do regret all of them to some extent. However, I have simply learned to be more careful what I buy. It is painful to part with any gun that you don't hate, however, we all have limited resources and I'd rather sell a gun I'm lukewarm over to get something that I will like. I will be restricting my sales to guns I don't like or that I'm lukewarm over and I'm sure I'll like what I'm replacing it with (and then only if I will be replacing it within the month and not "eventually"). Short of money, well I'll try to be sure that isn't a necessity again, but if it is I'll pick the least bad sale (one cheap to replace, one I don't use much anymore, one that is more or less a duplicate of something else or at least in the same catagory).