I love to wheel and deal. When it comes to guns, three transactions "take the cake" in my mind.
First was an old JC Higgins branded 20 ga. bolt action. I had just turned 18, and I was at the first auction where I could legally buy a gun. I bid and bid on an old Marlin .30-30, and thought I was going to take it home with me. Turns out somebody behind me won the bid. Determined to excercise my new status as an "adult" (if you can call an 18 year old American civilian boy that...), I wasn't going to leave without a gun in my name. I bought the shotgun for something like $60. It needed some TLC, so I lovingly refinished the wood and reblued the metal. And then I could not hit the broadside of a barn with the full choked tube. Down the river it went. Some time later, my dad and I were at a flea market. He was looking at some coyote stretchers, but the asking price was too high. Ended up trading the shotgun for all of the stretchers (which all told, had an asking value of something like $200, if I recall), AND I got some boot...to the tune of what I initially paid for the gun.
Second deal was sending another down the river. I had a basic "GI" 1911. New manufactured, so there was no collector value. Honestly, I just didn't care for this particular one. I love a 1911 (carry one daily), but this pistol and I...just didn't jive. Same flea market that I sold the 20ga at, a couple years later, and there was a small gun store. On this particular day, there was a Left-Handed Custom Savage .243 that was stunning. There was some scroll work on the bolt, action, and towards the muzzle, inlaid tastefully in gold. There was also a Marlin .30-30. Owner of the shop said I could have my pick between the two in exchange for the pistol. I himmed and I hawed, and decided to go for a walk to decide which was coming along with me. As beautiful as the .243 was, I thought the .30-30 would be more practical, as I did not have any centerfire rifles at that point in time. Having made up my mind, I returned for the trade. As fate would have it, another southpaw had picked up the .243 in the meantime, so it worked out. Initially I thought this was just a standard "Marlin .30-30"; that's all I knew, and all I wanted (I should say that I although my family hunts, I'm the only "gun guy". Growing up in a shotgun only state, I didn't have that much exposure to rifles, other than what I read in magazines, etc., as this was the dark ages before Gunbroker, Armslist, and well...the internet in our home). Turns out, I traded up quite a bit. What I traded into was a 1936 manufactured Marlin 1936 in DARN good original condition, save for a few wear marks and dings in the old walnut. I am not trying to brag on the old girl, for I had no idea what I lucked into, but EVERY one of my gunsmith friends (and I have several) have tried to get that old Marlin into their possession. Until I pass on, I'll keep this one close. It makes one fine carbine for still hunting or following the hounds here in the Appalachians.
My latest was my .375 H&H. I THINK I have shared the story here before, so I'll try to be brief (which can be a challenge for me). Prior to my first safari, I wanted a .375. DG was not on the menu, so it was not necesarry, but I WANTED one. Thing is, as mentioned, I'm a lefty. Not too many LH .375's floating around here in East TN. In a twist of divine intervention, I was out of town for work, and, whilst perusing Gunbroker one night in the hotel room, I came across a chap that had one listed. In the same town I was working in. I called him up, and he had not one, but FIFTEEN LH .375s in stock. Mauser actions. Turns out, he was one of two importers in the US. AND HE WAS WILLING TO TRADE for a pistol that I just so happened to have along with me. As mentioned, DG was not initally on the menu, but, because I had this rifle that I was led to, or it was led to me, I was able to harvest a lekker buffel.
I know that was windy, but each one of those three acquisitions stand out to me.