The really short version is that the kind of setup he wants the world to have is too unstable for the breadth of territory and interaction of cultures and politics.
(And honestly I often think that while GRRM was thinking Wars of the Roses, the actual interpersonal and inter-fiefdom shit he wants is actually suited to half a millennium earlier, in the Heptarchy, and that was even less centralized and less well organized and less integrated than the Wars of the Roses.)
The long version is . . . honestly quite long: it involves getting into the nitty-gritty of what logistically it takes to get large numbers of people to agree to follow basic sets of rules, to operate their world in the same way, to agree that this rule applies here and this rule applies here and even if those rules are unfair and unjust, to even apply them consistently. Have you ever tried to organize a community group to do something the same way? Like that except a million times more Plus Swords and Violence.
The kind of feudal vassal-overlord relationship set that's supposedly working in GoT is one that's personal and immediate and inevitably also breaks down into war every few generations (at the longest). By the time you're actually trying to work on the scale of people, institutions and mileage that's involved in GoT, you have to have institutions that outlast people.
They will probably still be some level of nepotistic/etc - I'm not saying that you end up with Perfect Fair Egalitarianism. But you can trace this progression in every large organized empire that lasts (and this is a crucial point) beyond one or two generations - and make no mistake, even Westeros itself is functionally an empire (that is: a centralized government ruling over a number of disparate and originally politically independent regions which were originally united by conquest). You have to be able to appoint someone who is basically competent to oversee things that need to be done; you can't rely purely on who inherits political power where. You also have to make sure they CAN'T just go "you know what? fuck this shit I'm out" with the whole of their army or they will do this . . . .at least once a reign.
(Even in England, York went through a period of basically doing this every new king. They were subdued! They swore allegiance to a king! . . . that king died and even though he was succeeded by his heir in quick and orderly fashion, York went "right, fuckit, fuck off, we're done!". . . . .and the new king had to go subdue them. And then he died and although he was succeeded in orderly fashion, York went - )
If you want Westeros to work, the royals have already so thoroughly intermarried and politically intertwined with the Starks that much like the duchies of York and so on just became parts of the English crown, titles and positions to be handed to certain levels of that government structure (like yes: those levels were "the blood heirs of the ruling monarch" but it's still just part of the government in a monarchy), Winterfell isn't a separate political entity just barely agreeing to be part of the whole thing with a totally separate lineage, Winterfell is an extension of the centralized royal family. Ditto everything else. Or you maybe still have local rulers allowed to do local things, but they're operating within the empire/centralized government under the supervision of a governor/proconsul/satrap/whatever you want to call them who arranges the centralized taxation and military drafts and so on.
And like: you're free to ignore all of this and have fun with the stories, don't get me wrong. "Shut up there's dragons, just let me have fun" is a valid position to take . . . as long as you slash the author do not then try to make claims for 'accuracy' or 'realism'.
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