Urban Survival 101
The following information is adapted from GURPS Dungeon Fantasy 2: Dungeons, written by Sean Punch and published by Steve Jackson Games.
Getting Stuff Cheap
The PC may attempt one of these activities per item. "Item” means one large article (weapon, magic item, etc.) or a group of small ones (e.g., a suit of armor or a quiver of arrows).
Scrounging: Success finds $5 worth of non-magical items. Critical success (ordinary success, for someone with Serendipity): a more valuable item (GM’s choice).
Bargain Hunting: Quick Contest of PCs Merchant skill vs. a generic Merchant skill of 15. If PC wins, 10% savings. If PC loses, price is 10% higher than usual. A tie results in retail price. PC may choose not to pay an inflated price but will be unable to find gear at a better price before the adventure begins.
Black Market: Streetwise to get something (usually cheaply) on the black market. Quick contest of PCs merchant skill vs generic Merchant skill of 15. PC may choose not to pay inflated price and still has the option of acquiring item legitimately. Critical failure with black market results in confiscation of cash or gear equal to 10% of starting wealth.
Shoplifting: Filch roll to steal any article that would fit under a shirt (3 lb maximum). Valuable items are watched carefully (-1 per doubling of $100+ value, additional -3 for anything rare or magical). Failure results in a beating (1d cr dmg) and confiscation of all gear. On successful Filch, thief must use Smuggling to get away clean.
Scoring Extra Cash
A PC can try each of the following activities once while in town before each adventure, or one of them daily while awaiting a quest
Dredging and Mud-Larking: Roll against Urban Survival to seek coin in gutters. Success finds $1 times margin of success, with critical success resulting in a valuable object (GM's choice). Critical failure results in a case of sewer rot.
Bumming, Busking, and Haranguing: Skills used are Panhandling, Dancing, Musical Instrument, Performance, Poetry, or Singing (if show includes music or song, also check Musical Composition). Players with multiple skills begin with their best skill, then roll once against any others, apply +1 per success or -1 per failure, then roll against the total. Success earns $2 times margin of success. A critical success scores a useful gift (GM's choice). Critical failure means a beating (1d cr dmg) and a broken musical instrument.
Gambling: Quick Contest of PC's Gambling skill vs. a generic skill of 12 for sums up to $25. With higher stakes, the opposing generic skill is increase +1 per doubling). If PC wins, double his money. Tie is breaking even, and a loss forfeits the PCs stake. Sleight of Hand may be used for cheating (success adds +3), but failure results in a severe beating (1d+3 cr dmg).
Working the Crowd: Pickpocket success nets $5 times margin of success. A critical success means $50 times the margin! Any failure results in a beating (1d HP). Critical failure indicates swift justice in the form of a broken hand (1d months to heal, barring magic).
Additional Information
Old Tarantia is not quite lawless, but neither the City Watch nor the King's Guard patrol the area (indeed, they rarely cross the river to the old city unless there is a riot or other civil unrest). The legal authority in the old city is the Office of the Justiciar, a private law enforcement agency supported by the merchants and other interested parties of Old Tarantia. The Justiciar's men do not patrol the city, but occupy headquarters near the East Gate. The may be summoned by ringing any of the various bells located in mercantile areas of Old Tarantia.
North of the river, the city is governed by law and order. The City Watch patrols the streets day and night, keeping an eye out for criminal activity as well as other forms of civil unrest. Those suspected of or captured in the commission of crimes will generally be incarcerated in the city dungeons until they pay a fine or are brought before a magistrate. Capital crimes (murder, rape, and excessive property theft or destruction) are heard in the King's Court. The rulings of magistrates and the King's Court are final and without appeal.