We gave my wife's oldest son a oak dining room table & chairs and sofa when he "needed" it.. When he moved out he left it all behind in the house he was sharing with his buds. It had zero value to him at that point I guess

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I would like to offer a different perspective.... when you said "at that point".... I think timing is everything.
When my Grandma died about 20 years ago, I was still in college, and working and moving a lot. My Mom asked if if I wanted her silverware, her coffee pot, her pyrex, her x-mas ornaments.... "no thanks Mom, I don't want to move that stuff around, and I don't want to add to my storage in your house" I said... My wife and I have since purchased all of these things, because "it is just like Grandmas. How I wish I would have said yes to mom...
About 5 years ago my Dad asked if I wanted his 1952 Chevy pick-up that he spent the last 4 years "restoring".... I judged his restoration to be slip-shod, and I would have had to drive and trailer it about 12 hours.... I said "no thanks Dad, you should just sell it, I don't have the room". I had just had my first child, just moved into a new house, just , just , just... so he just sold it. Dad died last month, I wish I had JUST said "yes"! He was proud of the piece of ****. I wish I would have said yes, maybe I'd be less of a piece of ****...
My mom ( she's 73) has started doing the "final-countdown-clean-out" ... although my wife gives me dirty looks, I have said yes to everything and I am putting in lots of time with all the junk moving and sorting. It is funny how when you are younger, you can't be burdened with all the crap, then you get middle aged, and the memories are locked into all the stuff.... then your own mortality smacks you in the face and you try to pass on the stuff, hoping that the memories pass too.... "value" has many measurements, don't be too hard on your wife's oldest son, blame the timing.