1. V is correct, Jakkonn WILL be on his ship. This is indisputable
2. Though Iron born longships are large, an Ironwood galley WILL destory one with a ram, especially if they are moving with the current.
3. Theon made the trip with 1 ship, that is a considerably quicker journey than 40 could make, I imagine that is probably an extra week AT LEAST
4. The iron fleet is indeed the elite force, only loyal and generally experienced raiders will be in it, meaning they will be hard fought to be defeated in ship to ship if they manage to board
5. That being said, Northman have it on solid ground, meaning the gurreila warfare will take a significant toll as you would not be able to counter attack. A psychological effect WOULD descend on the raiders after a week or so of this, as Iron Born are genrally less disciplined than other soldiers(We have seen this fact CONSTANTLY throughout the books and show), though I doubt deserters(they are on boats and experienced raiders), it will effect their sleep, and therefore their combat skills.
6. If Jakkon fights Tormin on boat Jakkon=win, IN A FAIR FIGHT. If Jakkon is outnumbered, for any reason, he will most likely lose(but take some Northman with him)
7. With 40 ships, none ironwood, two weeks travel up river, little to no wind assistance, I would guess around 10 ships will be lost to the arrows/other attacks of rangers, maybe a few less. One or two may have issues, such as crushed by a tree or run ashore as a result.
8. IN ACTUAL BATTLE
Iron born are better sailors and ship to ship combat, however by now ARE at least somewhat demoralized
They are most likely also outnumbered, leading to further demoralization.m m
Ironwood galley = better than an Ironborn longship, larger by a noticeable amount, tougher due to material, if up to speed will crush a longship, not splinters but sink ,taking armored Iron born(they have balls and do in fact where heavier armor on deck) to drowning death.
Longships better at maneuvering WILL board several galleys, take fight to northerners, will most likely win these exchanges. IF THEY WERE IN TOP SHAPE
They are not
The soldiers have been unable to fight rangers, will be tired from sleepless nights, not at their peak
Northerners are fresh, ready and on the defensive
I imagine an iron to north win loss ratio at 50-50, or 55-45, or posiibly 60-40
Ironborn are outnumbered, numbers WILL start to make a difference
We have seen Iron men betray commanders and run before, real commanders not Theon(A Humble is murdered by a fellow Iron man when Boltons come to town)
It may take a bit, but as numbers start to show, at least a few ships will most likely flee back down river, and Ironborn will see this and start to join. Jakkon and crew will not, to proud-to scared of captain whatever.
MOST LIKELY OUTCOME OF BATTLE
EXTREMELY hard fought northern victoy.
Expect sunken galleys, loss of men, general loss of life and resources, but Iron fleet there fleeingm and severely crippled.
Jakkon most likely captured or just killed(All it takes is one fall off boat and Jakkon drowns, plate and deep water do not mix)
I feel the post about the lead up and actual battle does require editing, but I believe a northern victory is likely, if a costly victory. Jakkon will most likely be captured.
I'm sorry, but from what I have researched this is how it is, Tormin may even be dead, it is a HELL of a fight. But remember 1 ship moves a LOT faster than 40, loyal or not, and the north has more ships in the lake, especially once Rangers exact their toll.
(Also add like... another 5 days to sailing from ranger interference)
No blodbath(except a mutual one), no slaughter, a hard fight with a pyyrhic victory is what I see.