The Nightsong Guild
The Nightsong Guild has worked within the city for as long as most people can remember—and probably a good deal longer. Its members deal in matters not entirely legal as well as those quite clearly illegal—gambling, smuggling, blackmail, and theft. The guild's reputation is one of extreme skill and competence. It is not feared as much as it is afforded the respect that it has earned. Most would refer to the Nightsong Guild as a thieves guild, but it is actually a far more extensive group than that. Its membership includes rogues, fighters, bards, wizards, and sorcerers.
Guild members do not take part in violent activities such as extortion or murder, for the guild V leadership has long maintained that if you kill or intimidate your clientele, those people cease to League of make money (and if they don't have money, the Boot and Trail guild can't make money). Of course, if one or more of its members are attacked or threatened with violence, the guild is quite clearly capable of dealing with the situation.
Joining the Nightsong Guild: Slow to add new members, the Nightsong Guild prefers to work with those it considers potential recruits for several years before actually inviting them to join. Candidates serve as paid informants, freelance burglars, or muscle for hire for long periods of time while their competence and trustworthiness are judged. Although most of these recruits are never told explicitly that they're working for the Nightsong Guild, the group is powerful and notorious enough that most individuals guess correctly where their money comes from.
Members are required to contribute 10% of their earnings to the guild. In return, they have access to extensive resources (see below).
Character Benefits: Within the confines of its home city, the Nightsong Guild can offer its members nearly impenetrable security, well-funded political connections and access to well-trained and loyal hirelings or followers. Members also have access to the guild's extensive library, training facilities, and workshops. Many places of business in the city offer 10% discounts on services, goods, and equipment to Nightsong Guild members.
These resources can be incredibly useful, but they come with a price. As an efficient and long-lived criminal organization, the Nightsong Guild finds a profit in every activity that it undertakes. If the guild provides a PC with access to a local baron and guarantees that the baron listens to her request, the guild requires in turn that the character undertake a dangerous mission to further cement that baron's willingness to obey the wishes of the guild.
Roleplaying Suggestions: Highly trained and supremely confident, members of the Nightsong Guild remain calm and professional even in the most intense circumstances. They work best in unified teams, and they make a habit of knowing their companions' strengths and weaknesses. They expect quick and competent action from their allies, especially in combat or on a dangerous mission. This combination of expertise and trust makes most members reserved and stable individuals, and they rarely waste words on trivial matters or debate. When a guild team or adventuring group makes a decision, the member is likely to keep her opinion in reserve until she has heard arguments from several other members, speak up once, and then quickly act on whatever decision is reached by the leader or by consensus.
Typical Member: Most members of the Nightsong Guild are low-level rogues, experts, fighters, or warriors. The rogues and experts serve as the eyes and ears of the organization, and the best and most loyal eventually advance to become members of either the nightsong infiltrator or nightsong enforcer prestige class.
Prestige Classes: The Nightsong Guild includes members with levels in an eclectic collection of prestige classes, but most belong to the nightsong infiltrator or nightsong enforcer classes. These two prestige classes epitomize the organization of the guild itself. Two-thirds of the group, led by the nightsong infiltrators, spy on the rich and noble, ferret out secrets for use in blackmail, perform daring acts of burglary, and attempt to divert the efforts of law enforcement. The remaining one-third of the guild's membership, led by the nightsong enforcers, provides the group with the muscle that it needs to protect itself.
Lore of the Guild: Lenias D'Brule, noblewoman, adventurer, and one of the few powerful members of the Nightsong Guild who is open about her guild membership, has recently disappeared. The guild would like this problem to go away permanently. Either Lenias must be found and convinced to tone down her high-profile lifestyle, or the guild must be certain that she will never surface again. Because the guild is busy with its own interests in the city, a few representatives are quietly approaching established adventuring groups to find the noblewoman, deal with those who caused her disappearance, and then confront Lenias herself.
A Nightsong Guild Campaign: Although exceptions exist, the Nightsong Guild shouldn't become a major feature in a campaign until the player characters reach at least 3rd or 4th level. That's because until they've completed a few adventures or missions, they're not likely to attract the attention of the guild. Once they've achieved at least a small amount of success, an adventuring party could find the Nightsong Guild to be an intriguing and powerful patron - or a dangerous and resourceful enemy.
Sample Nightsong Guild Member
Alyson Adair: Female halfling rogue 1/fighter 2; CR 3; Small humanoid; HD 1d6+1 plus 2d10+1; hp 19; Init +7; Spd 20 ft.; AC 18, touch 14, flat-footed 15; Base Atk +2; Grp -1; Atk or Full Atk +7 melee (1d4+1/18-20, masterwork rapier) or +7 ranged (1d8/19-20, masterwork heavy crossbow); SA sneak attack +1d6; SQ trap-finding; AL NE; SV Fort +4, Ref +5, Will +3 (+5 against fear); Str 12, Dex 17, Con 12, Int 10, Wis 13, Cha 8.
Skills and Feats: Balance +7, Climb +9, Hide +11, Intimidate +5, Jump +2, Listen +9, Move Silently +9, Spot +3, Tumble +7; Alertness, Improved Initiative, Iron Will, Weapon Finesse.
Languages: Common, Halfling.
Sneak Attack (Ex): Alyson deals an extra 1d6 points of damage on any successful attack against flat-footed or flanked targets, or against a target that has been denied its Dexterity bonus for any reason. This damage also applies to ranged attacks against targets up to 30 feet away. Creatures with concealment, creatures without discernible anatomies, and creatures immune to extra damage from critical nits are illumination all immune to sneak attacks. Alyson can choose symbol to deliver nonlethal damage with her sneak attack, but only when using a weapon designed for that purpose, such as a sap (blackjack).
Trapfinding (Ex): Alyson can find, disarm, or bypass traps with a DC of 20 or higher. She can use the Search skill to find, and the Disable Device skill to disarm, magic traps (DC 25 + the level of the spell used to create it). If her Disable Device result exceeds the trap's DC by 10 or more, she discovers how to bypass the trap without triggering or disarming it.
Possessions: Mithral shirt, masterwork rapier, master-work heavy crossbow with 20 bolts, 2 potions of cure light wounds, 30 gp.