[Hungkung]

My first response to the OP's question, is yes it can be done, but choose your race wisely, Cey, kindly gave an answer of which race to choose to only be KOS in 1 city, and dwarf faction is pretty easy to get once you get into the newbie area (not that hard, but you probbaly know that)

I got to lvl 200 diplo and still a lvl 4 adventurer, before my brains leeked out my nose and I had to do something else. The only thing I found really daunting was the presence grinding, where it just wouldn't go up sometimes...I wonder if they make viagra for presence, or is presence what viagra is for?

the money isn't actually that bad, for what you're doing, nearly always 9c a parley in reward, unless you get the rumor's/etc and then you can sell the extra diplo clothing you get so for the risk on that aspect it's excellent. and you don't bruise your ego or chestplate getting killed very often.