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Yeah I'm an Imperial yet I helped the Stormcloaks who said they were happy with anyone to join their cause. Also if you go to Windhelm someone mentions that Ulfric tolerates everybody but favors the Nords.
As for the questions Im pretty sure there aren't any benefits unique to one side other...
Other than the fancy store in Solitude, is there just a place to buy normal clothes? I'd like a hood other than the mage ones and I can't find any place to get one.