One more reason to leave it alone to his war games.

Again this thread derailed into a pro/vs Stormcloacks and Imperials.

The original question was: is Ulfric a good strategist?

Ulfric is a natural born leader and fine warrior but, that doesn't make him a good strategist. He's overly confident that might in battle and bold actions will win the war but, other than that, he doesn't strike me as a brilliant commander. It doesn't help that his second in command is thick as a stone (pun intended)

what I think everyone is forgetting is that it is a CEASEFIRE meaning that for the time being there will be no fighting. So ulfric is free to move as much silver around as he wants until the fighting restarts and by that time the windhelm coffers should be nice and full anyway

How long is the ceasefire in effect though, there's a lot of ground to cover and things to organize, would take weeks, (or even longer - what is the lore size of skyrim meant to be?) to march from Markarth to Windhelm, and that still doesn't mean the Imperials couldn't play nasty and hire people to watch the roads.

Even if their is a ceasefire, I doubt that the Stormcloaks could move supplies through Imperial territories without violating the agreement. The silver could be smuggled across, but if the Imperials can ambush Ulfric and his top lieutenants in Stormcloak territory, they can easily target a couple convoys of silver in Imperial territory.

"They have an abundance of gold and silver, and these make war, like other things, go smoothly"-Hermocrates
Without the resources to fund a campaign, the campaign will fail. That is why your great generals often try to seize the resources first. Look at Trajan in Dacia, taking its mines to fund campaigns in the East, or Hitler trying to take the Caucasus Oil Fields. Not only does it keep your own men in the field, it also prevents your enemies from doing the same, and is therefore the best logistical move (and therefore the best strategic move) Ulfric could make.
Furthermore the Reach is a hard land to fight on, and would certainly slow down the Stormcloaks in their fighting, as the Empire has a greater pool of resources and manpower and can fight a war of attrition, whereas the Stormcloaks need a lightning victory.
In terms of getting resources to and from The Reach, it wouldn't be too difficult to go through Whiterun, which is essentially neutral in the conflict. I doubt they'd intervene, and they'd be unable to in force, without substantial help from the Legion, in which case it is more likely to create a full battle in the hold.
Additionally, Ulfric could just take Whiterun, like he'd planned.