DracoSuave said:
It was around the time where he mentioned attacking Whiterun for no other reason than because the Jarl was more concerned with the impending dragon invasion rather than the Civil War that I began questioning everything.
Actually, Ulfric Stormcloak doesn't 'attack Whiterun for no reason.'
Whiterun is in the middle of Skyrim, and a buffer between the East (which has solidly pro-Imperial Jarls) and the West (which has solidly pro-Stormcloak Jarls.) The other holds aren't 'stepping stones to Solitude', they're Jarls who support the widow for the office of High King. With the land so evenly divided, the Moot to determine High King would be at a standstill, meaning actual war is inevitable. And Skyrim NEEDS a High King at a time when OH GOD DRAGONS EVERYWHERE.
So, Ulfric approached the one Jarl who was the swing vote with the offering of his axe, essentially forcing the one fence-sitter to choose: Keep the Axe, meaning he's willing to fight for Ulfric, or return the axe, meaning they are not allied.
Whiterun doesn't get attacked for no reason; it gets attacked because doing so leads to the end of civil war.
Remember, Ulfric challenged the High King according to Nordic law, and the king accepted the challenge, and his reasons are just; Skyrim needs strong leadership, and the High King was not strong leadership.