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It would appear as though your likely romance option is going to be Viconia, unless you try to keep a moderate reputation so you can balance Aerie's and Edwin's happiness and then woo the whiney wingless one. Be mindful of your PC's race if you're going for a romance and you haven't got a modded game.
I agree with Kyravias that a warrior of some sort would probably be the go - something like a dual classed Assassin-Fighter could work well as could a Swashbuckler, although in my view the most powerful option would be the Fighter/Thief multiclass where you can access a wide range of HLAs.
As for alignment, I'd go Evil for use of Blackrazor if you're not going to get the rogue's 'Use Any Item' HLA.
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