I think for a north putting together an economic development plan, a western fleet like you proposed is crucial. On the other hand, a fleet just sitting around doing nothing during peace loses money and there’s not much trade opportunities for a northern merchant fleet since westerner and reacher merchants are better positioned. So, trying to circumnavigate the planet is a must for any northern economic development plan in my opinion. It’s either the riches of the east or an unspoiled continent.

I don’t agree that “there’s not much trade opportunities for a northern merchant fleet.” If there’s enough trade opportunities for the hardscrabble Iron Islands to have an active port town doing business from southern Westeros and Essos both:

“The Myraham was a fat-bellied southron merchanter up from Oldtown, carrying wine and cloth and seed to trade for iron ore…A handful of Lordsport merchants had gathered to meet the ship. They shouted questions as the Myraham was tying up. “We’re out of Oldtown,” the captain called down, “bearing apples and oranges, wines from the Arbor, feathers from the Summer Isles. I have pepper, woven leathers, a bolt of Myrish lace, mirrors for milady, a pair of Oldtown woodharps sweet as any you ever heard…”

“…Theon was more interested in ships than gods. Among the masts of countless fishing boats, he spied a Tyroshi trading galley off-loading beside a lumbering Ibbenese cog with her black-tarred hull.”

“…She had surrendered her virtue at six-and-ten, to a beautiful blond-haired sailor on a trading galley up from Lys.” 

then there’s no reason that the vast agricultural markets of the North just on the other side of the Flint Cliffs from Ironman’s Bay, wouldn’t find buyers from among the ships that sail the northern stretches of the Sunset Sea.

By contrast, trying to sail west across the Sunset Sea has historically been a fool’s venture:

“Strange tales like this are common at the edges of the world, however, and the Lonely Light stands farthest west of all the lands known to us. Many a bold mariner has sailed beyond the light of its beacon over the centuries, seeking the fabled paradise said to lie over the horizon, but the sailors who return (many do not) speak only of boundless grey oceans stretching on and on forever.”

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