TypicalFicEnjoyer6
I don't see any way that MC can be one of the main parties in the War of the Five Kings, and I also see no point in developing a worthless place like this one year before a war that will eat green and dry, Shouldn't you focus on developing a profitable trade to equip your troops with the best equipment, at least that's how you'll be in the best of Negotiating the price of joining a certain party.
TypicalFicEnjoyer6:*Spoilers* Crackclaw point may be poor but it is easy to defend and hard to attack. Note that when the Andals tried to conquer Crackclaw point, they were defeated. And this is just the start (Spoilers again) at the later chapters, mc already have a army strong enough to take the Vale (SPOILERS THE THIRD TIME), in which he did.
Building a port now!! is good but should have been put forth years ago or creating basic military training for soldiers these things if done could have increased his house's strength. But not enough to incur job arryn to action or incuraged more Smith's or anything 1 year to grow is never gonna be enough. City's and ports and armys and Navy's take many years to make even with 10s of thousands of people.