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Message: <blockquote data-quote="Camelot" data-source="post: 5142798" data-attributes="member: 82617">Definitely go with your number three, I think.  Multiple small skill challenges give a fun sense of progression, while one long skill challenge, unless it is very multilayered (see the DMG2, chapter 3), gets boring. Make sure to tell your players right off the bat that there is no way to defeat the beasts simply by fighting.  Something like, "Bugs and vermin burst forth from the sewers all over the town!  There are billions of them swarming the city.  People start panicking as they are attacked by the violent creatures.  There's so many of them that it would be impossible to fight them all; you'll have to focus your efforts on getting the civilians to safety."  Then give them their options: kids in a wagon, merchants behind locked doors, etc.  If they fail the skill challenge, then have them go into an easy fight against some of the vermin., worth the same amount of XP as the challenge would have been. Coincedentally, I homebrewed some cockroaches a while ago.  If you need some roach monsters, since I don't believe there are any in the official books, you can find them at my blog, The Dungeon's Dragon, in the post of Resistant Roaches.</blockquote>