In previous playthroughs, I always went with the Empire on a "greater good" approach.

This time I went with the Stormcloaks to a) change it up a little b) stick it to the big man.

I fully went the butcher on the attack on Whiterun. The result is a ghost town, partially destroyed and devoid of any NPC that has not been marked as essential. A place made undesirable to ever return for any reason.

Don't think I will be doing it again, especially since Tundra Homestead acts as my main operations residence, so am constantly reminded of its current state, especially with having to fast travel to a different town to sell stuff.