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... In summary, all these assumptions are quite strange, and points 2 and 3 are complete nonsense.
Please suggest your move for Gurney. The army isn't particularly strong, but there are funds available: move towards the red faction, scout, grab resources if you find something valuable, and pay them off; if you don't find anything, try to pay them off and return home. You're essentially suggesting jumping back into the dungeon, and playing that way means you might as well surrender immediately, because sooner or later the blue faction will become strong enough to come and visit. The end goal is the same, but the first option is much more efficient. It's a risk, but you can't win the game without taking risks when you're in such a difficult situation, so Oelm is right that hiding in your spawn points and being afraid of shackles is foolish. Regarding a favorable trade: considering Neela's attack and defense, which are visible in the tavern, it's quite logical that the trade in the first round will be favorable due to the implied bonus of 1000+.