Well, lets see. Yep, I'd do some things different if I had it to do all over again. I'd skip my 2 boys and go straight to grand kids! They're lots more fun and someone else's primary responsibility. I do know that I'm having a lot more fun with my 1 YO grandson than I ever remember with any of the others. We have a family friend who's in her mid 70s. Saw here last month and talked with her. She asked how many grand kids I had now, so I told her 7. She already knew which one I liked the best. The littlest one, of course. And the only way that can change is for another one to come along.
OK, guns. I'm only 65 and I've been thinnin' the herd for about 10 years now. Still doin it, too. The first rule is if you've got a gun you want to go to someone, give it to them as soon as they're old enough and responsible enough to understand. If that little one of mine keeps charming grandpa, he'll have a bunch of fine guns!

I had family guns. Those went to my boys. Its not that I didn't like them, it was just too much responsibility for me to bother with. Besides, my father was pretty practical. I'm not, so I buy the guns I want, not the cheap ones.
I gave up on me buyin so much ammo to last the rest of my life. I'm workin on buyin enough for the little guy to shoot for the next 80 years, too! The problem with holdin on to every thing till I take the dirt nap is how's momma gonna handle gettin rid of it? Here in America, its a time honored tradition to cheat women's and orphans. If they take a $5000 shotgun down to the flea market or local gun store cheaters, she'd be lucky to get $500. Them boys is thieves.
Of course I'm not the brightest bulb, either. I know, I spent thousands on a lousy old revolver. You can get a brand stinkin' new Taurus for under $500. I've had personal occasion to watch a great collection get dumped on the market. A big time collector up and died. His widow did call the local to them gunshop. They came in and did a complete inventory and then offered to buy the whole mess for $200,000. The widow was way too smart to do that. So she sat on the collection for a few more years, then got David Carroll to sell it on commission. And she got several times as much. They've got to earn a good living at a gun store.

When my gun show partner croaked in 2007, that same store cheated the living daylights out of his widow. And they were all supposed to be good friends. I guess at least they didn't cheat her any worse than someone off the street.
My ignorant wife had a plan. She was just going to let the boys come in and pick what they wanted (cherry pick) and then sell the rest. Its a formula for disaster. None of my guns have any real family background. They already have those guns. My guns are the one's I like. But they'll probably bring a good buck when sold by the right person. And its not just guns. What's she goin to do with the Randall and Gil Hibben knives? Every one knows cheap ole hunting knives are only worth $10 or so each, right.
And in all this, I realize the friends I have probably couldn't even price some of my treasures. The worst deal to get involved in is doing a widow a favor and try to sell her junk. Widows seem to come in two flavors, the ones who hate the stuff and would give it away, and the ones who think Hubby was the smartest guy in the world and think everyone is trying to cheat them. Don't even show them a value guide or Fladermans. Those fools can't even get the model numbers right in their book. And it takes a couple of years to get the thing written and published.
I could go on for hours.