I think you may have hit the nail on the head. I am fairly new at this, so I am going to try to hold onto all of mine. I have been tempted to trade this or that. Probably a bad idea. I have good memories with them all.
Sold a Sears marked Stevens 311A .410 years ago I wish I had back. I have the rest, and would like to see it returned...especially if I can give what I got for it.
Once in the 80's I needed money and sold one of my Great Grandfathers' shotguns. Regretted it ever since. If faced with the same situation again, I would sell a kidney before that gun.
A few years ago I sold a VERY MINT Marlin 39A Mountie 1962(my year of birth) vintage lever action rifle.And now for the life of me I do not even remember the gun I bought with the money? But I do remember the 39A Mountie. Stupid, stupid, stupid me.
I regret both guns I've ever sold. Especially since I ended up basically replacing them with newer (slightly better) versions of themselves. I also regret not taking some of the guns my ex and I bought while he was deployed (FFL transferred in my name )
Springfield Loaded Champion I sold because of a Motorcycle payment being due and being short on cash (missed a week of work with the flu ). To top it all off, I sold the bike 6 months later. Regret it so much I am in the market for one as we speak!
I've sold several, but wouldn't buy em back if it was available. Only exceptions are a Smith 442, Walther PPS and a Smith 22a. All three I sold for way too cheap and all three were guns I liked, but sold when I bought a house that needed a ton of work and I needed some cash. I'd buy those guns back for the price I sold em for, though I doubt that would ever happen.
However, regret selling? Nope. I spent the money on indoor plumbing which is a lot more useful than a couple guns in the safe. Just regret selling too cheap, losing about 150/gun.
I am really sorry for the Model 66 that was stolen from me it was one fine Smith. Now it is hard to find one that they don't want a lot of money for. Now the Glock 19 didn't like it the day after I got it glad it is gone. Went to Walter and love both the 9mm and .40 both are great.
Sold it last fall cause I thought I didn't really need it. Then my friends and family all wanted to do Appleseeds this year and I miss that little guy!
Replaced it with a cheap Model 64 but the length of pull is very long and awkward for my fiance to use and they don't make a replacement stock as far as I know. I sure miss the collapsible butt stock on the 15-22, but I'm not going to pay $550 to replace it.
I've only had a few regrets for trading or getting rid of couple of the firearms, but I have benefited by doing so for bigger and better. I have gotten to the point of keeping most if not all of what i have and if there is something I want that they will only take trade ill find one buy one trade one. I would never trade or sale firearms that have been in my family could never do that.