Reading Storm of Swords and on Jon's last chapter before he leaves the wildlings.
I always found this passage so interesting. It (sort of) drops the title of the final book, shows a dream of Jon's, and brings up some interesting logistical questions.
His lord father had once talked about raising new lords and settling them in the abandoned holdfasts as a shield against wildlings. The plan would have required the Watch to yield back a large part of the Gift, but his uncle Benjen believed the Lord Commander could be won around, so long as the new lordlings paid taxes to Castle Black rather than Winterfell. "It is a dream for spring, though," Lord Eddard had said. "Even the promise of land will not lure men north with a winter coming on."
If winter had come and gone more quickly and spring had followed in its turn, I might have been chosen to hold one of these towers in my father's name. Lord Eddard was dead, however, his brother Benjen lost; the shield they dreamt together would never be forged.
I've always understood the traditional hierarchy as overlord > vassal > miscellaneous lords. So Winterfell rules and collects taxes from the Glovers/Manderlys/Karstarks who rule and collect taxes from the minor lordlings in their domains.
So what exactly would the process be for raising new lords? The Starks could send a bastard son, as well as any of the other major vassals with bastards. And Maybe Ned offers some land to the mountain clans or something, but what about after that? Would they give a holdfast to loyal retainers like Rodrick Cassel? Does Winterfell go to each vassal and say "give me your best minor lordling"? Or do they just open it American frontier style and if you can claim it, it's yours?