The youngest generation I know that still played "old-school" is my generation (born 1979). My younger brothers don't have the same sentimental attachment as I do regarding that style of gaming. It should be no surprise, it is all a matter of timing after all. It was only around the early 90s DnD really got a more solid footing here in the Philippines. There is that cultural comprehension and economic requirement to have access to the hobby. We were the friends of the younger brothers of the younger members who initially got into it.
Looking back, Old school rules are funny. When I learned more about the world and furthered my education the design of the system can look very haphazard. Well It was, I'm not going to beat a dead horse about it. Although there is some fun to be had expounding the premises to their absurd conclusions.
Reductio ad absurdum is when one argues a premise to its logical absurd conclusion. It can also be funny. One of my favorite is when I look at the Thief and his abilities: why is it the thief can do certain things functionally better than anybody else is a good exercise of absurdity.
Looking at the old-school spells, abilities, races and classes with (Utility-Cost /Time) x Odds is also another way to look at all the old DnD. I find the scariest min-maxer is an adept game-theorist, with the skill of breaking things down to pure utility and who can do the math mentally.
I'm really looking forward to having some of the Freethinkers have a crack at Old School.