I'm a Nord leaning towards the Imperials, so far. I haven't completed any quests to fully join them, though. I may switch to Stormcloaks and save the Imperials for my next play through with a different race.
my first play through I didn't choose a side, just did the main quest line (redguard)
my 2nd and 3rd playthroughs are undecided, but probably one for each just to see the stories played out
although I do not like Ulfric's racism and how he kills his own people who don't agree with him. I also don't like how the imperials are just thalmor puppets
Considering the Elder Scrolls lore following the end of Oblivion, the Imperials are pretty much ruined and in shambles anyways, and they've failed to recover the Empire. So I went Stormcloaks, because someone needs to pick up the pieces.
Stormcloaks for sneaky play through (though, I honestly left it alone for a long time as I am tending to play the "what's in it for me" role with this one), and will be going imperial for my orc warrior.
Comments
my 2nd and 3rd playthroughs are undecided, but probably one for each just to see the stories played out