Burglar
Skill Progression: The vital skills of a Burglar are Open Locks, Find/Remove Traps, Move Silently, Hide in Shadows, Detect Noise and Climb Walls. As mentioned before, a Burglar may concentrate particularly on one of these, but he would probably then want to be as evenly excellent as possible in the others.
A specialized thief is simply more marketable. People in the underworld want someone excellent for a job. That may mean a high-level generalized thief, one who has been in the business long enough to be good at everything. But it's not easy for a thief to reach that level. Therefore, by concentrating on one skill, a relatively low-level thief may compete with a thief many levels higher for jobs of a certain type.
Suppose, for instance, we have a "box-man" - actually a woman - named Annelise. By concentrating as many points as possible in her open locks skill, she can have a score of 85% at only 4th level (this does not include modifiers for race, Dexterity, armor or kit). Since she can put no more than half of what she earns at each level into any one skill, she distributes her remaining points more or less evenly among the other skills. She would probably neglect pick pockets and read languages, however, since they usually are not useful to a Burglar.
Compare this to a "generalist" thief, which adventurers tend to be: On Table 19 of the Dungeon Master's Guide (Thief Average Ability Table), you can see that Annelise's level of lockpicking skill would not be attained before 14th level.
Now imagine that a mob of jewel thieves is preparing for a job. They have diverse skills - except that they are lousy at lock-picking. They need to bring a box-man into their mob. Who would they choose? Well, first off, a 14th-level thief is pretty bloody rare.
And even if one were available and willing to work with less-experienced thieves, he would probably demand a larger share of the take. Otherwise it would not be worth his time: He has uniformly good skills, and could probably commit this robbery on his own. A job with which he would need assistance is probably well out of the range of these thieves.
Annelise, then, is a pretty attractive option. She might be able to climb little better than a fish, but that's the cat Burglar's expertise; after he's mounted the building, he can lower a rope for the less sure-footed. By offering Annelise a reasonable share of the loot, the other Burglars are almost assured that their difficult lock will be opened.
Other Burglars specialize by target. Jewel thieves in particular are the elite among Burglars; the protection found around the objects of their attention demands that their skills and cleverness be honed to perfection.
Burglars of any background may be found. Even thrillseekers of the privileged classes may take up jewel Burglary as a challenging, profitable, and exciting pastime.
Almost all successful Burglars have some sort of guild affiliation. In order to get rid of the loot they take, they of course need a Fence(especially if their score is distinctive - e.g., fabulous gems, valuable artwork).
Guilds provide the Burglar with innumerable benefits: fencing of even the most distinctive items, connections with potential "business" partners, access to specialized equipment, and, not least of all, protection. A guild can arrange the fix (to free an imprisoned Burglar), and provide deterrence, protecting its Burglars from other guilds and powerful criminals - people who don't take kindly to being robbed themselves, and are more likely to make hasty decisions about a suspect character's guilt or innocence.
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