Hypothetically, if Robb had won the war and married Roslin Frey, who would have been tw best internal marriage options for Edmure and Sansa to help integrate the two portions of Robb’s kingdom?

Assuming that Robb doesn’t need external alliances, it would be a good idea to marry Edmure into the Manderlys – they’re a powerful Northern House, but they’re also the most conversant with Southern culture of any of Robb’s original bannermen. Moreover, their naval and commercial presence at White Harbor would enhance North-Riverlands connections if properly exploited. 

As for Sansa, I’m not sure who I would handle. But one idea that does come to me is for Robb to settle Harrenhal on her – Harrenhal is going to be incredibly important for him holding the Riverlands from attacks from the south, so a Stark presence there will probably be necessary for making it actually perform. 

In your EDPs, you recommend city charters in every one of the regions (except maybe the Iron Islands). The question is: Why would any Lord Paramount (or the King) encourage the creation of such charters? You wrote in response to one ask (long ago) that these charters made the residents “free burghers rather than serfs or vassals”, “the city/town and its residents were no longer part of a feudal fief, and thus didn’t have to pay feudal taxes”, etc.

There’s a couple reasons. 

First and foremost, money. While the residents themselves don’t pay feudal taxes (or sometimes fewer of them, or only to the liege lord rather than the whole chain of subinfeudation), the people who travel to the town aren’t afforded the same luxury. And since cities are hubs for trade, there’s a lot of money to be made from import duties, port fees, warehousing fees, and other taxes. 

Second, goods and services. Aside from your village blacksmiths or village carpenters or whatever, the vast majority of peasants are engaged in the production of agricultural goods and other raw materials. Cities, on the other hand, is where you get specialized manufacturing on larger scales – textiles, metalworks, glass, etc. A domestic source for these kind of goods means that it’s cheaper to get those kinds of goods for yourself, and it means a more favorable balance of trade for the goods you can’t get at home. So to put your military cap on for a minute, if you’re trying to equip an army, cities with their more advanced economies are invaluable. 

Third, political organization. While this is potentially a double-edged sword for feudal lords, one of the advantages of having cities is that they govern themselves to some extent. This means that the lord, who already has to administer a fief with an extremely limited staff, doesn’t have to spend time governing them and has someone on the ground they can turn to enforce laws for them. For example, you’re probably going to be able to raise more in taxes (or payments in lieu of taxes) than you would from the peasants under your own control and with less effort, because people are more willing to pay when they’re taxing themselves. Likewise, a city or town militia means higher-quality infantry – at the very least, you know they’ve done some drilling and have standard equipment – than your standard peasant levy.