Hmm... more settlements that could be added..
The Vale: Old Anchor, Wickeden, Bloody Gate, Ironoaks
Westerlands: Cornfield, Starsfield, Feastfires, Deep Den, Ashemark (as I stated before
)
the Reach: Longtable, Grassy vale, Red Lake (all these to House Tyrell) Bandallon (To House Hightower). Also I say give Honeyholt and Uplands to House Tyrell, Hightower is too powerful in my opinion. Even more then Tyrell, since they have Oldtown... which in my opinion is the coolest city in Westeros
The Iron Islands: Lordsport (as I stated before), Shatterstone, Blacktyde, Synderly. (You will probably have to expand the isles a bit) I think there should be a castle in every isle, although that in some isles there are more then one... but since Greyjoys are probably the weakest house in the seven kingdoms I think only one castle in every isle. I am not sure if all thse 4 settlements should be added... to keep Greyjoys weak in comparison to other houses, I think either add Lordsport or the 3 other castles.
Dorne: Vaith, Ghaston Grey (to add Ghaston Grey you must expand the very small isle in the Sea of Dorne) Ghost Hill, (all these to House Martell) Blackmont (to House Yronwood). Also, move Kingsgrave to it's correct location, it is supposed to be in the horizantal pass between Yronwood and Skyreach... see pic. Also, I think that Skyreach should be a settlement of House Yronwood.... just my thought's
the North: Already added a ton of new settlements, I only think you should add Hornwood to House Bolton, as some members said it's a good idea
Crownlands, Stormlands and Riverlands have already even more settlements then they should have
so no need to add any more there.
I also think that all the
really really crappy and small castles you added in the Stormlands should be Motte and Baile's. That is also what I think you should make the small settlements I suggested you should add in the Iron Isles - like Synderly and Shatterstone. Blacktyde is a bit bigger, so make it a wooden castle.
Also, maybe you can add a mechanism so that Houses whom are vessals of a cerain house - (for example Redwyne to House Tyrell) would agree to be vessals of said faction if it is offered to them by a diplomat.