DnD: Perilous Procession #5 - Gain Entrance

Wow, here we are at the end of my very first set of skill challenges! For some reason, I thought I had six challenges for this, but it turns out there were only five. So, presented here for your enjoyment, the final chapter of the Perilous Procession:

#5 - Gain Entrance

The PC's have decided to use the caravan as a means of gaining entrance to a fortified city or town they might otherwise not have access to (as opposed to trying to force their way in or sneaking in by some other route). However, the guards have been warned to be on the lookout for a group of adventurers trying to sneak past them and are wary of anyone trying to gain access to the city.

Encounter Level
PC Level + 2

Complexity
2 (6 successes before 3 failures)

Primary Skills

• Bluff (Hard DC)
  Do you want to be the one to go before the city council and explain that their harvest festival was ruined because you didn't like the way a couple of farmers were dressed?
  
  • After first failure, subsequent uses of this skill auto-fail for that PC, -2 for other PCs to use
    
    
• Diplomacy (Easy DC)
  In a perfect world we would all be walking around with three forms of official documentation. I'm willing to bet that you yourself have less than that on your person. What I do have is a desire to see your fair city, boost the local economy and carry abroad tales of an enjoyable visit.
  
  
• Insight (Moderate DC)
  I can tell you really don't enjoy wasting your day standing around out here. How 'bout we buy you a drink when your shift is over?
  
  
• Intimidation (Hard DC)
  I suggest you let us through. Our oxen have been known to get spooked by unwarranted searches and I'd hate for you to get trampled.
  
  • After first failure, subsequent uses of this skill auto-fail for that PC, -2 for other PCs to use
    
    
• Streetwise (Moderate DC)
  Look, Devlan, is it? I happen to know that you're tight with a close acquaintance of mine. A certain merchant of hard-to-procure items and experiences? Ask him, he'll vouch for me. I might even convince him to give you a deal.
  

Success - the caravan is allowed inside the city walls
Failure - the caravan (along w/the PC's) is refused entrance, caravan annoyed with PC's
Critical Failure (less than 50% overall success before failure) - the ruse is discovered and the PC's are attacked/captured