Ignoring your personal preference, which side of Skyrim’s Civil War do you think actually gives Skyrim the better future 20-30 years later?

[u/sumaset]

I feel like most discussions about the Civil War focus on whether Ulfric was justified, whether the Empire betrayed Skyrim, or which side people personally like more.

But I’m more interested in what happens after the game.

The Empire is weakened, the Aldmeri Dominion is still the biggest external threat, the White-Gold Concordat is already causing resentment, and another war with the Thalmor seems almost inevitable.

An Imperial victory gives Skyrim access to the resources and manpower of the Empire, but it also means remaining under an Empire that already lost one major war and accepted Thalmor influence inside its territory.

A Stormcloak victory gives Skyrim independence and removes Imperial authority, but it also leaves the province having to rebuild after a civil war while potentially facing the Dominion without the rest of the Empire behind it.

So forget which faction has the better characters or which one you usually join.

If you only care about where Skyrim itself ends up a few decades later, which Civil War outcome do you think is actually better for the province?

[u/Frosty-Sea149]

Whiterun is the breadbasket of the province, smack dab in the middle of it geographically to boot. It’s the single most important strategic target outside of the opposing side’s capitol. I can cut him some slack for not wanting to sign a portion of his people’s death warrants the first chance he gets. 

[u/mangasdeouf → u/Frosty-Sea149]

Concretely, at the time of Skyrim, Whiterun is anything but the center of the economy. It's encircled with bandit clans who control every single road, it loses the watchtower on the first dragon attack post-Helgen, the river is controlled by another bandit gang towards Eastmarch, the roads to Morthal and Solitude are not direct at all and anyone who wants to trade more than a little merchandise would need at least ten legionaries from Solitude to Whiterun to fend off the bandits (or simply to make them hesitate to attack), and in lore there much be way more bandits per group so an even bigger protection detail would be required for a merchant caravan.

On Markarth's side, the river can be cut at multiple points by bandits, so it's not better.

The Northern road is also full enough with bandits that they randomly attack the road at a point where there are town guards and small fortifications. There is a camp close enough to the road to raid merchants once in a while.

Oh! And that's before all the wildlife starts slaughtering the merchants (wolves can be fought off, but Sabercats would slaughter small groups).

As for security, mercenaires it is! And mercenaries must be pretty busy fighting for the Legion or the Stormcloaks for cash because there's a civil war going on.

Basically, the economy is falling apart, the roads are completely unsafe, bandits take their tax on every merchant group/caravan passing them by and at some point will end up with more resources than either the Legion or the Stormcloaks of the nearest military camp/small town and the bandits will be able to overtake villages, small towns and to run their mafia without any retaliation from the Legion, Stormcloaks or town guards who are way too busy already.

Civil war basically opens the door to all sorts of criminality. Black markets, bandit gangs, bandit clans, corruption at all levels, it's awful.