I don't have anything super collectible, but some OK stuff I take hunting.
My MZ is a TC Hawken Silver Elite, not too common a rig. Paid $315 back in '95 or so (can remember the price, but not the year). I could get over 500 for it (but since I took a buck that was in the 170's gross, 160's net, naw it aint goin' anywhere).
My two deer handguns are an E series Python and a 3 screw SBH. The latter I recently got, just 'cause I like 'em (had others). My dad bought the Colt around '72 and I grew up shooting it. Got it for my BD a few years back. Box, papers........it's worth way more than what he paid for it back then used. Got holster wear, and I hunt with it (one 8 pt and one coyote so far).
It simply isn't for sale. None of my colts are. They will go to my kids, with the stipulation that they have to be passed to blood relatives, lest I come back from the grave as the rudest poltergeist ever.
Rarely do I buy and flip for making $. Over the years I've lost some here and there, made a little once in a while, score sheet is about even. But I used my stuff, took good care of it and when I changed my mind or wanted something else, I sold at prime time.
Always smart to buy out of season. Doing that has allowed me to shoot and hunt with a variety of items over the years, on a limited budget.
I've seen other folks who can't manage their money buy and then have to sell, over and over........lose substantial amounts each time. I think one dude sold and bought back his nothing special 10/22 at my LGS 5 times, they cut him some slack the last few times, whenever that "bad penny" showed up (sometimes somebody else bought it and it was gone for months. No, not a pawn deal..............just one guy who went back and forth.
And he is not an uncommon type of customer. Oh well, they keep the gun and pawn shops open.
IMHO the more I pay for something, the more I need to shoot it
Been on rough times and sold stuff before (Big D) but hey, I didn't lose $ on that stuff even when in a pinch.
Heck, I just bought a gun to kinda sorta look like one my dad has, and yeah it was a little under priced (good deal). I fully intended to hunt it, keep it...........but after checking around, nope............I can probably triple my $ on it (did not think it worth that much-suprise).
On stuff I'm not in love with.............yeah I'll let stuff go for that