Christmas Presents to Give on Chanukah

“I recall seeing in Emes L’Yaakov that the original/initial minhag was gelt, ”

you recall correctly . Though he says gifts are ok too (unlike others he knew shava kesef kekesef)
Also see his Son R’ Ezreil Aurbach sefer Avnei Yashfeh chelek1.

“How this evolved into ipafs, bicycles, video games, etc. is beyond me ”
It isnt so complicated, I’m not sure why you are having a hard time at all understanding it.
1) Kids (young ones) are more excited by presents than money.
2) the goyim around us give gifts this time of year and there is a theme of “gift giving” that has spread. As the saying goes Vi es kristelt zich azoy men yidelt zich.
This is really isnt a hrad thing to understand, and I would question calling anyone a talmid chacham if they had any trouble understanding these 2 basic points, let alone if it being “beyond” you.

Now, as to whether point #2 would make it assur, THAt is a legitimate concern. I Again invite you to live up to your name and read the very short siman in YD.

“and a lot of other talmidei chachomim”
there is no talmid chacham that I am aware of who has trouble with this point. IT really is simple.
Yes accordign to the Gra it may be assur and that is obviosuly valid (not that he needs my haskama) but cmon learn a little, easy with the silliness .

“Shava kesef kekesef! Are you for real?”

ITs wild but its true! See the first mishan in Kidushin I was surprised too! how do we even know such a thing? Tosfos says it s a limud from eved ivri and nezek, the Ran says its a sevara imagine that?!!

“Next time i buy an item at Pomegranate for $2.50, i will hand the cashier a copy of that day’s issue of the anti semitic New York Times!”

Well, no because you cant acquire food wit h kesef nor shava kesef. but as for house or even a wife yo u can absolutely acquire them with a copy of that day’s issue of the anti semitic New York Times!
Of course she has to agree. and if the owner of pomegranate agrees to accept the NY times, then you can in fact pay for an item with it and acquire it with say hagbaah

Minyan challippin?