Troubleshooter
Skill Progression: Picking pockets and reading languages are not of much value to the Troubleshooter, but he will probably seek a fairly even distribution among the other thief skills.
Troubleshooters are rarely guild members, naturally enough, unless they have been bought off in exchange for information on the clients they've served. Of course, few such Troubleshooters will survive long; if they give a place's security their "seal of approval," and then it is broken into with ease, the Troubleshooter's reputation will be shot, and he can expect to have more than a little suspicion placed on his shoulders.
While everything going wrong has its ironic professional advantage, the downside is of course that the things that go wrong often do so to the Troubleshooter's personal disadvantage. This is difficult to quantify, to define as a game mechanic. Instead, the DM is encouraged to bring it in at his discretion during play, for maximum excitement and role-playing fun. Fill the character's life with astronomically improbable events and bizarre coincidences.
The DM is by and large left on his own to "wing it" with this special benefit/hindrance, but there are two questions for him to ask himself before he brings it into play: Would this further the plot of the adventure? Would it be fun? At least the second question should be answered "yes," and it is best if both are.
Furthermore, the rule to follow in deciding the specifics is: Everything should be balanced. For every freakish mishap that works in the Troubleshooter's favor, there should be a complementary one that works to his disadvantage.
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