I wear business shirts that require cufflinks, double cuff shirts, and have many cool cufflinks but it's the ones I've been given that mean the most.
You ask me a tough question...
I think l, like you, there's a lot of things I'd like to hand down some of value and others not.
My Rolex watch would hand down as would my gold and silver, but I have a hunting knife that would need to go as well, I have a few awards and accolades that I would like to hand down also, just for posterity's sake. I have the stuff of my dad and grandad of course and a few other things.
I guess the most important thing would be my skills, values and ethos. I'd I had a son or daughter and that's all I left then I'd be content.