When the Riverpullers Guild blockaded Romney over a conflict with the craft guilds, Waylander was caught on the wrong side of the blockade. Unsuccessful in negotiating with the leader of the Riverpullers, whom he terms "a hard old crat," Waylander has been fighting to reenter the city.
Supporters of the Riverpullers consider Waylander a "snake" for failing to support them against the upstart Guild of the Romney.
Waylander can be found watching the bridge to Romney, preparing to leave for a meeting with associates in Sloop. He warns the party how seriously the guilds are taking the siege and explains its background politics, mentioning that only skilled hagglers have been able to stay in business during the price hike. Seigneur Locklear agrees with him that the Riverpullers' actions threaten Romney's rights as an independent Kingdom town, but Waylander notes that the Duke has been unable to act against the labor guild as yet.
If the party returns later in the chapter, Waylander is pleased to find that the Riverpullers have not harmed them. He reports that he has found some support among Glazer's Guild members in Sloop, but is unsure when or how much help they will send and hope it becomes unnecessary to count on them.
The party may ask Waylander for negotiation tips. To offset the monetary losses of a delayed arrival in Sloop, he charges 50 sovereigns for the lesson; if they refuse, he offers again after his trip southward. Agreeing provides a one-time boost to the party's Haggling stat. Waylander's advice includes:
- Avoid appearing lordly or aggressive while haggling, leaving arms loose rather than folding them, and feign uncertainty to humanize oneself and encourage generosity;
- Maintain eye contact to suggest shared interests and disarm others by inviting them to feel authoritative;
- Never interrupt the other person;
- Insults and factual arguments disrupt the bargaining atmosphere, which relies on a tacit agreement that both parties are acting in good faith; appearing less interested in a high price or low offer is more likely to encourage a change for the better.
With the guild feud still simmering, Waylander has blocked the bridge to Romney to prevent undesirable arrivals from touching off a full-scale guild war. They permit residents free passage, but restrict strangers from entering without a Glazer's Guild Seal as proof that they have been vouched for.
Waylander explains the situation and confirms that the King's men have arrived from Bas-Tyra, but has no reliable way to contact their leader, mentioning that they are elusive and untrusting. He tells the party that the Guild seal they need to enter the city is hard to come by, mentioning an unruly group of would-be Guild members unable to find a sponsor due to their behavior, but confirms that possession of a seal would grant them entry. As the party departs to find one, James asks Waylander to tell the King's men that "three men" will shortly consult them about "a nocturnal bird that kills at night".