So I'm already starting to think about my next character... So with a few mods installed I think I can achieve a really interesting play though... A Dumner... A refugee from Morrowind arrives in Windhelm... He works the docs... the farms anything for a few septims so he can have a hot meal and some ale... He lives rough in the Grey Quarters like so many others like him... (Better Grey Quarters) Most nights he hears drunken xenophobes hurl obscenities all hours of the night... But little do they know a resistance is forming... On the face of it the new Gnisis Conerclub is a place where Dunmer piss away their Septims... First they plot their revenge on the people of Windhelm but it soon evolves into a secret fight against the Stormcloaks...

So that's the idea... I was wondering is anyone knew of any quests that could help me... My mind's drawn a blank...

I sort of did that with the one character I played through the Dark Brotherhood. It's just that he chose that organisation to do so, rather than try and make a new one. And eventually he joined the Imperial Legion, as only a player that does so gets to kill his main target.

DB + Legion may seem contradictory, but for a Dunmer it can make sense, as he ends up getting his revenge on both Nords and Imperials.

I think that'll happen eventually but because I RP he wouldn't just join the DB straight off the boat... It has to happen organically... So really looking for little quests that could nudge him in that direction...

You can leap in directly if he's reached Windhelm already. You'll get the Aretino boy rumor from anyone there. Maybe some other excuse to go to Riften is all you'd need to continue, and radiant quests like Queen Freydis' sword may do that if the location chosen is in that direction.