I’m skeptical of any negotiations with the ironborn in terms of marriage alliances or political alliances, such as the popular idea of Robb marrying Asha if he keeps his hand open. They seem so culturally other (especially in POV chapters from the Greyjoys) that it seems they would be incredibly fickle. The best scenario would be something akin to the Red Kraken where his nominal allies just let him attack their enemies and hope for the best without any higher strategic considerations.

Culturally other – I dunno. Depends which era of Ironborn you’re talking about. Plenty of Ironborn Kings traded and treatied and married with greenland houses, for periods that lasted for centuries at a time. 

So if Balon was more like Quellon, or not in the picture, I could see Robb/Asha working well for both sides. 

How would the politics and War of the Five Kings change if Lord Walder Frey had died before the series started?

Interesting question. I suppose it depends on how quickly things go to hell in a handbasket – obviously, Black Walder is still going to make his move, but he has to kill his way past a lot of Freys. Ser Stevron is the new Lord and he’s got three sons and seven grandsons. 

Also depends on whether the Freys are there for the disaster beneath the walls of Riverrun, and if they are, whether they get away intact (as I think the Mallisters did). 

The first major difference would come with Robb’s arrival at the Twins – Stevron doesn’t have the sheer chutzpah to extort Robb, so he probably lets him cross without all the marriage stuff. Which means Robb’s hand is open for negotiations with the Iron Islands, Dorne, or Highgarden post-Renly, and there’s not the same excuse for the Red Wedding as in OTL.

However, for all that Stevron is a generally standup guy, he’s also generally very cautious when it comes to matters of grand strategy (he was the one saying that Robb should let the Baratheons and Lannisters fight it out and bend the knee to the winner), so he’d probably still pull out of Robb’s army if as in OTL the Tyrells allied with the Lannisters. However, it would be far more low-key and less murderously damaging than the Red Wedding. 

What happens if Aenys Blackfyre is granted safe passage and presents his claim to the Great Council of 233 AC?

Hard to say. Blackfyre strength was certainly on the wane after the Third Rebellion, but on the other hand the pickings were pretty slim at the Great Council. I suppose the major question is how attractive a candidate Aenys would have been, both in his person and his policies. For example, could he have promised and delivered on an end to the Blackfyre Rebellions?

Probably not. Given that Daemon III, as the son of Haegon, would have considered his uncle a usurper and had the Golden Company to back it up, I don’t think Aenys could have delivered on peace. 

You mentioned in an earlier response that Tyrion didn’t really have an alternate path if he wanted to get out after Tywin vetoes the inheritance. But it seems like he was planning that anyways, in his last conversation with Sansa – talking about how it would be very wise for him to get as far away as possible from King’s Landing when Joffrey outgrows his regency, including to the Free Cities. What’s the difference, other than time?

Preparation. Tyrion would have needed to take a lot of money with him to the Free Cities. Also, there’s a difference between Tyrion leaving the family and breaking relations with Tywin and taking a diplomatic trip to the Free Cities to stay away from Joffrey. 

Tywin would probably have accepted the latter, certainly it would have made his job easier, and would have funded Tyrion in the style of a Lannister to avoid shaming the family name, etc. 

Pre-Aegon, who out of the Tullys and Tyrells would have had more prestige respect and power. I’m thinking the Tullys because what they had was theirs, they had land, a castle, they were a very old house dating back longer than the Tyrells. But would the Tyrells connection and marriage into the Gardeners elevate them in anyway?

House Tully would probably have more prestige, because they were an ancient house and had their own lands and title.

But House Tyrell definitely had more power. As High Stewards of the Reach, they were the right-hand men to the Gardener Kings, and exercised enormous influence over the kingdom. While Tyrells were Regents of the Reach during the minority of Garland VI, I think the more instructive example was Ser Osmund Tyrell. Following the death of Garth X and the Manderly-Peake civil war, Ser Osmund got 40 houses to follow his lead, put down the Manderlys and the Peakes, and chose the next King of the Reach. 

So even before the Field of Fire, the Tyrells had become the power behind the throne. 

That last ask got me thinking, especially as I’m on ASOS in my current reread. Once the battle of the Blackwater is done and Tywin vetoes the Casterly Rock inheritance, why doesn’t Tyrion get out? All his support is gone everyone else wants him dead, and Shae’s never more than a minor mistake away from losing her head. Why not get away from all this and go back to his life of women, wine and books?

Because women, wine, and books cost money, and Tyrion doesn’t have any outside of his family. It goes back to what Tyrion said when he and Jon were on the Kingsroad to Castle Black: “if I had been born a peasant, they might have left me to die.”

Tyrion doesn’t fit very well into the economy of a feudal society – without an inheritance from House Lannister, he’s not going to have an estate that provides him an income. He’s not physically capable of performing the labor that makes up 90%+ of the labor market (although a market in labor doesn’t really exist at this time). He’s literate, but he’s not a maester, so he’s got a credentials problem. He’s a skilled politician and administrator, but given that those positions are filled based on blood ties and/or the patronage of liege lord to vassal, as a political nobody he’s not going to get an appointment as a steward or anything. 

At best, Tyrion might be able to eke out a living as a scribe or clerk in some merchant’s office, but he’s not going to be able to afford much of wine, women, and books on a clerk’s salary.

In ADWD, we see how precarious the life of a dwarf on his own can be with how quickly and easily Tyrion is thrown into slavery, and from the example of Penny’s precarious existence. It’s only by extreme luck and his own cunning that he’s found a place in a mercenary band rather than dying in a fighting pit as an undercard amusement. 

Rhoynish remind me of the Gauls and Celts who fought the Romans, fierce but motley and disorganized. Had they stayed in Essos and after the Doom of Valyria, could they have stopped expansion of Volantis and the Slave Cities and defeat the Dothraki?

Probably not. Keep in mind, Nymeria’s ships were filled with desperate refugees, the fighting strength of the Rhoynish had perished at Volon Therys, and the victorious Volantines and Valyrians were settling down. If they had stayed in Essos, they would have all been enslaved as Druselka and her followers were when they turned back to return to Mother Rhoyne. 

Given the scale of enslavement that followed the Rhoynish Wars, the majority of the people who live along the river today are likely Rhoynish in ethnicity, but the Volantines still rule. For now…