I sold a couple but don't necessarily regret it. I had an early Rem 700 BDL 7 Rem Mag that I bought new the first year I was in the Army in 72. Used it for several years but it never was a great shooter and I sold it to my oldest brother. He shot several moose with it and a couple deer and passed it down to his son when he quit hunting, so it is still in the family and I see it occasionally during deer season.
Also sold my first rifle to another nephew- a Savage 340 30-30 that I took my first couple deer with. Don't really regret selling either of those rifles to be honest..
The ones I regret selling weren't even my rifles. My inlaws were hurting for money in the 80s and so was I. There was no work and I had a young family to support and couldn't find work no matter how much I tried. So, my inlaws asked me to try to sell my Father in Law's rifles to put some money together for bills they were late on. There was a Trap Door Springfield 45-70, a Mauser 96 6.5 x 55, a beat up old .22 of some denomination that was totally forgettable and the two I hated to sell- a Win 92 in 44-40 Rifle with factory double set triggers and a Marlin 39A in good, but not great shape.
Sold the 39A to a friend for a very fair price at the time and he still has it. I've tried to buy it back a few times but he isn't one to let go of his guns . However, most of my FIL's guns were home gunsmith specials, including the 92 Winchester .which had several extra holes in the side of the receiver for home made side mounts for scopes over the years and other alterations that severely altered its value. But it was still a very rare and cool rifle- a rifle in what was at the time considered a target round in what was considered a target rifle. I would have kept it and had it repaired, welded up the swiss cheese action, and gotten the non working double set triggers fixed, but at the time there just wasn't the money to spare. The gun shop owner I sold the 92 and the Springfield to was a good friend and he gave me very fair prices for both of them so let them go and gave the money to my FIL.
