Oh sure.
I had a Valmet O/U shotgun. got bored & sold it. Then saw it for sale again for sale, regretted selling and bought it back. Then I patterned it and discovered why I never could hit anything with it. One barrel patterned about 18 inches high at 30 yards. The other was maybe 6 inches high. I re-sold it and don't want another.
I can think of 3-4 rifles I sold that I wish I still had. The worst was probably a Rodda Field's Patent Falling Block .500-450 single shot from 1890 or so. It was heavily worn, but I now know people who could fix it. I keep hoping to see it turn up at an auction somewhere, but no dice.
