Duel vs single, depends on if your making your own gear for which to go for.
if your making your own gear, then duel wield since 2 weapons can hold twice the enchantment of one weapon.
If your using premade non uber gear, then the choice might still be for duel wield if you want to focus on defence - since as a rogue, you would want to wear the monk boots (thereby not having haste from boots of speed) and you would want to wear the wizards robe (dmg resistance), that leaves just the offhand for a haste weapon.
If you want greater offense however using premade gear, then you would want to go for a two handed weapon with the various feats that make it powerful.
As for the class, id go with a 19 monk 1 rogue (save up the points from the monks leveling and dump into rogue skills at level 20).
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