That is an interesting question. Due to sentimental value, I think my last gun to keep would be the Phoenix Arms HP22 pistol my father has. It was the very first firearm I had ever fired when I was perhaps 7 or 8 years old and it was the gun he used to teach me how to handle firearms safely and how to shoot. The mere sight of that pistol brings back many a fond memory of the countless hours spent at the gun range punching paper, busting up dirt clumps, or knocking over spinning targets. I estimate we have fired over 20,000 rounds through that gun in the 25+ years I have been shooting with my father. Numerous parts have been replaced and it is on its 2nd or 3rd replacement barrel, but it keeps running just fine. It is not worth much at all, probably less than $50, had dents and dings on it, and likely has permanent powder burns, but to me, it is a gun that holds a special value that no other firearm can match.
Out of the guns in my collection, I would be torn between my Colt Python, the R9, and my Remington 870. Each fulfills a certain purpose and both the Python and 870 have special meaning to me. The R9 is hard to give up simply because it is my EDC pocket gun. Given your previous mention of having had to use your R9 in a defensive manner, I think I would favor my R9 as well. As they say, the best gun in the world is the one you have on you when you need it most!
