Isn't there an 'include lower titles' option when you give away land that grants the entire thing?
That's what I was saying that didn't work. Just gives them a single county in the kingdom and the title.
I have literally hundreds of baronies to sift through and a desire for some organization. Initially I started handing out counties with single holdings, then two holdings and so on, which were spread out all over. All the vassals have -20 penalties for various Duchies and Kingdom titles so even if I do give them all enough land to reduce the penalty for "needs more grazing land!" or whatever they all hate me 'cause they're spread out everywhere.
It only became a problem when I got Conclave though. Everybody would get all pissy about my conquesting without the Council's blessing and I may have not noticed that for a while and then wondered why literally every single person in my glorious land loathed me with a passion before realizing.
"Oh," I said "Looks like a reign of tyranny is going to begin." before demanding titles from all the non-nomad vassals, then imprisoning traitorous bastard nomad vassals and then the problem I have with handing out land.
TL;DR doesn't work, multiple -20 "I want
x title" penalties, Conclave, not paying attention to Council's opinion on starting wars, reign of tyranny, mass demand on non-nomad vassal titles, imprison and murder nomad vassals, too much land to sift through for order, can't hand it out with organization 'cause doesn't work.