Was disarming (banning the owning/carrying of weapons) the commoner-class an actually policy in the middle ages? I see it in other fantasy works, and it seems strange to disarm men you are very likely to be calling on to fight for you.

Depends very much on the time and place, and whether the establishment saw armed peasants as a military asset or a threat to the social hierarchy.. 

For example, the English monarchy did the opposite – the Assize of Arms of 1182 and 1252 made it a legal obligation for all adult men to own and maintain arms and armor (with the longbow as a minimum requirement by the latter law) so that they could be called up to fight for the King (with the exception of Jews, who were commanded to sell their arms and armor), and Edward III’s decree of 1363 required all adult men to practice archery. 

By contrast, in the 15th century, it was illegal for peasants to carry weapons without royal permission in Sweden, following a revolt against the Union of Kalmar. In Germany following the Great Peasants War, many jurisdictions banned large numbers of former rebels (sometimes entire communities) from owning weapons. In Japan, the famous “sword hunts” of Oda Nobunaga and Toyotomi Hideyoshi disarmed the peasantry, especially the largely peasant warrior-monks who had so threatened the power of the samurai. 

Do you think Tywin plotted with Denys Darklyn to lure Aryes to Duskendale? It seems ridiculous that Darklyn would risk the extinction of his House over a charter.

If so, it would have been incredibly risky – given how badly Lord Darklyn wanted that charter, why not sell out the Hand who’s not getting on with the King in the hopes that you get that charter as a reward from the King? 

If Tywin had a plan, I think it was a lot simpler. From the WOIAF, the beginning of the Defiance is described thusly:

“It was Lord Denys’s desire to win a charter for Duskendale…this did not seem to him such a vast demand…yet it was understandable that Lord Tywin, as Hand, firmly rejected his proposals…infuriated at the refusal, Lord Darklyn then devised a new plan.”

Why did Lord Darklyn think it was an easy lift, and then get so pissed off when he got turned down? One possibility is that Darklyn had been told ahead of time by a deniable intermediary that everything was kosher, to raise his hopes and increase the chances of a rash reaction. 

Then all Tywin would have to do is to work a little bit of reverse psychology on Aerys II. 

Do you think the First Great Council was a sham? It seems likely that Jaehaerys favored Viserys and knew that most lords would also so I think he wanted to add legitimacy to the claim by putting it to a council, as well as satisfy his own conciliatory urges. If push came to shove I’m sure Jaehaerys, a universally revered king, could have forced the issue if he had to and there would not have been serious push-back outside of the Velaryons and maybe Alyssane.

No, I think the point was to gain consensus. Even Aegon, who very much forced a lot of issues, knew he had to be acclaimed by his vassals to be recognized as king.

Jaehaerys wanted to make sure that no one contested the succession, because under his reign there were a lot of Targaryens with dragons. This way, he could show any potential alternative monarchs that they would be going up against the whole of the realm. 

How realistic is the Iron Island’s drastically different culture? I was looking at the map and I just realized just how close to Westeros they are; Bear Island and Tarth are both farther away than Pyke or Harlaw are. It doesn’t seem really plausible for such a unique culture to form so close to the Riverlands while other islands are representative of their region

Well, the distance between the court of Charlesmagne at Aachen and the pagan Danes was less than 400 miles, but the cultural differences between the Carolingian Empire and the Vikings was far more extreme than the difference between the Ironborn and the Riverlands. 

A quick online search says that the role of cup-bearer was a high office. Nobles and kings have been cup-bearers to emperors, and the position entailed a great deal of risk on the cup-bearer’s part (they sometimes tasted the wine) and esteem from the person they were bearing cups for. If this is accurate, is it historically inaccurate for nobles in Westeros to take children and have them serve as cup-bearer? Or was this a position given to high-ranked up-and-comers?

He’s sort of mixing two different offices – cupbearer and page. As anyone who’s familiar with Crusader Kings II knows, cupbearer is an important office that you can give to men or women, which is handy if you’re trying to improve your wife’s opinion of you so you can start making some heirs. 

Pages, however, were noble male children in service to a knight or lord. And among their many duties might be to bring their knight or lord food or drink as request. 

So GRRM simply combined the two, because he wanted a way for Arya to overhear Roose Bolton. 

A common theme with stuff like the peasants in TSS and Meribald’s experience in the Stepstones is that the common soldier is often going to war woefully underequipped. Is this a phenomenon that has been exaggerated by Martin? I’ve been doing some nonfiction reading on medieval history, and it seems like it wasn’t too much of a hardship for common soldiers or even peasant levies to acquire proper weapons like swords or spears (if not up to the standards of weapons used by lords or knights).

It was a real phenomenon, but it’s also one that’s been exaggerated. 

While peasant levies did exist and tended to be not as well equipped, they didn’t really need to be. Spear and shield and helmet will do the job most times, and once you get into longbows, then your peasant levies are actually hugely valuable without the need for plate armor or horses.

Moreover, as time went on, you started to get specialization. Professional men-at-arms who could bring the equipment and skills of a knight to the infantry were hired with cash that kings raised from taxes in lieu of military service, mercenary companies emerged to deal with the slowness of pulling together feudal armies, and so on.