Oblivion gates are totally randomised, which also means you can get in the same one twice. Oblivion gates are seriously boring anyway, enter small tower, go up, enter big tower, go through Dark Salvation, Rending Halls etc., take Sigil Stone >.<
And everyone in the Tavern is supposed to fight. Isn't there a guard on a bench outside, aswell as one inside? If not, look for the Horse patrol, Wait till it's passing, kill the guy you want and run back outside, the Horse patrol should find you.
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