On Christmas day of my 16th year, my dad gave me a Savage 20ga pump as a gift. It was a shocker since my dad was pretty anti-gun at the time. The next day I learned my best friend's dad had convinced him to get it for me because "every man needs his own squirrel gun". A few years later I was really needing cash to get started in life, so it and a couple other guns went bye-bye. Fast forward another decade and I was in the final stages of a nasty divorce. The soon to be ex had done everything in her power to bury me financially. I had a decent WW2 equipment and weapons collection that would bring in a nice sum of money. So it along with my M1 Garand and GI bringback P38 Walther were liquidated. I suppose they all went to helping me along the way, but I surely would love to have that old Savage and my M1 back. Of all the guns I've bought, sold and traded over the years those are the only two that I really miss.
Pop gave me an Ithaca 49 single shot when I was 10 or so. Damn rear sight was canted, and I couldn't get pop to help me with it. In my frustration I sold it for peanuts. Wish I hadn't done that. Just found a rightly priced replacement within this last year.
Few years ago sold a beautiful p6 and an even better 239. I have found a stock p6 to replace the old one, but no such luck with a 239. Yet.
My S&W M66 snubby and my M45 Firestar. I sold them both to fund other projects and regret it to this day. That M66 was the sweetest revolver I've ever owned, and the Firestar was a great pistol. Oh well, live and learn.
I traded a xd .45 for a motorcycle(it was a complete basket case). It wasn't anything special but It was one of the first handguns I had ever bought. Definitely regret that one
My 1944 Mosin Nagant M44 carbine. It was made in the Tula factory, man was that thing a boss! took down a few Coyotes, ground hogs, and even a squirrel (that was messy). I bought it from Wannamaker Guns for $90 and sold it for $100.
Regret selling my Marlin Model 60, my first .22, loved that gun. Going to find one just like it again soon. Stupid. Don''t get me started on old cars I foolishly sold...