While it's true Skyrim's economy needs an improvement, I don't think we will ever see something so specific like you suggested. However if they made a better, living economy, those things would be easier to do.
I think cities that align with the Stormcloaks should have slower and poorer economies (less barter gold, less items for sale), since the Empire controls the trade through the Cyrodiil border and have ample patrols throughout Skyrim. The towns siding with the Empire would be thriving in trade. As the war progresses, things could switch, with Stormcloaks possibly high jacking caravans.
It'd be nice to see, perhaps in the next TES, other NPCs shopping in stores. See that helmet you want? Better snatch it up before some Merc visits town and buys it before you do...
As it is now, and as it has been, the stores are merely a place to dump loot. Maybe a merchant wouldn't buy that Glass warhammer you found, because the market is down, and no one would buy it. You'd have to visit another town. Of course the Khajiit caravans would still be around, and they could buy everything, so long as they had the gold.
That's what I'd like to see, anyway.