I’ll just speak to the kid piece. Or try anyway. I was lucky enough to be able to collect with my son from age about 5-12ish when we could go to Target and pick up product, buy him and my nieces booster boxes to break during family get togethers, and open current product. He would trade, sometimes getting ripped off by older kids, and we worked through some life lessons and there were many Christmas’ I helped rectify his bad trades, give him advent calendar packs to open, help him with supplies like top loaders and binders, etc. Building core memories around the cards, which he loved for a good 7 years. Some of his friends shared his collecting journey with him. I participated but let him guide what we collected together.
Shortly after he completed a masterful few binders of cards he loved, including cards before his time I added for him that he liked, he basically lost interest. I took his binders and cards and stored them away. I stashed extra booster boxes from what he opened with his cousins and have not touched them. I gave him slabs from my grading forays and he kept them in a carry case. Also stored away.
Recently he picked out some slabs he was ok selling and bought his first car with that money. Everything else is being held for him. He knows I’ve continued collecting, but he’s not interested except to say it was because of him that I started and he’s right. I’d have just stuck to the video games which of course he and I played. I also reminded him I only have one S/M Love Birds card because he said he didn’t like the card so I only bought and graded one for myself!
He got to show his own interest, build his own collection, and I got to be Santa to him and my nieces. I have no idea where the cards I own stand in his memories. But I did pick out slabs that are already very expensive to give to him and my nieces that I think they’ll like and won’t be able to afford for at least a while. They are now 1/1 in my collection, no doubles—Crystal Lugia, Karen’s Umbreon, Love Birds, etc. Expensive, iconic, mostly vintage. They are getting those cards, also all the sealed product to hopefully open together again someday. Or not, up to them. Not sure when to transfer the cards to them, but I’m not changing my mind or selling any of them no matter how high they go. I have some semi grails I fully expect to sell for life enrichment. I also have about 150 cards that are special to me that I won’t sell. Some very expensive, some not as much. My wife or son can decide what to do with them when the time comes. All the rest of the cards?? Man you got me. Do my best to sell when the time is right I guess. The beauty is slabs take up very little space. The bad part is the monetary value can’t be just ignored anymore. They are a liability and an albatross to me in many ways.
My advice would be to hold a few big guns back as inheritance since even many PSA 9s will probably be crazy expensive in the future. If your kid ends up collecting, he will help guide your purchases for his collection. Decide what to sell for quality of life now, and try and sell the highest ceiling cards last. Decide which cards to never sell as “Dads cards” your kid will always associate with you. If you sell a big card for say $100-$500k now that goes parabolic later, make sure it went to a good cause and don’t look back. The others will make up for it.
I agree we have a responsibility to try and make smart decisions since these cards have value NOW that the future doesn’t guarantee will hold. We also know you have cards you might feel sick selling too early now. Cover as many bases as you can and know you will take some Ls with the Ws. It sounds to me like you need to diversify from within your collection and yes, that means you have to let that grip go or you are too at risk of all or nothing. Shoot for 75% win. In my mind the only unacceptable outcome is to crap out when RIGHT NOW you are in the black at the table everyone wants a seat at. Don’t be a hero, Billy.