GAH! Insane Robbers!

[Fualkner Asiniti]

The party I DM is a rat's nest of irresponsibility and thievery. Lotsa fun to run. I am looking for suggestions on how to run their random robberies off-the-cuff. What sort of challenges should I give, treasure, ect. They like to pull heists as well as pickpocketing. Or should I say, bumping into and striping everything of value off of the nearest NPC.

[goat]

Random NPC = Level (partyaverage+5) rogue who counter-thieves as much as possible then runs.

[Bitzeralisis]

Try to have them steal from a random guy, then reveal that that random guy was actually somebody very important.. with lots of bodyguards and hired assassins...

[Icewalker]

My group did that once, and it was fun because one guy loved overly elaborate plans. Here's what it was:

Relatively rich noblewoman, has a small manor in town, across the street from a big museum, having a party, has a nice and slightly magical tiara they decide to go for. They manage to get one of their party hired as a guard, as each guard gets an amulet that calls down the guard captain (high enough level they didn't want to fight him) and they had him do that while the rest swung down a grappling hook line from the museum, broke in, left some false tracks, and made their getaway.

[Mr. Moogle]

Four words: Old Grany With Shotgun

She could maby say something like "HEY YOU, ROBBER PEOPLE" *party turns around to see a old grandma holding a ludicrusly large shotgun* "Get the F*** outa my house"

[Weirdlet]

That screams 'opposing thieves' guild' to me- whether they find a competitor on a job who keeps snitching things before they do, or end up robbing the manor of the wealthy head of the guild, or they get noticed by the local crime syndicate and get to encounter a couple warnings and finally full-out assassination attempts, they just gotta meet some prior theives' guild that isn't happy about them. Or maybe tests them for potentially joining up.

[Stormcrow]

Make them watch your right hand so they don't see your left.

You'd be surprised how many PCs don't see a set up coming. Advertise a large exhibition of some well wicked magic/valuable doo-dad that you know they'll be dying to steal and then have the guards be waiting for them. Its an obvious set up. Gives you lots of "escape from jail" and "conscript or jail" stories.

[illyrus]

To build off of Stormcrow's post:
I did a low level one shot of a bank robbery about two years ago. The PCs learned of some gems owned by the royal family coming thru town under fairly heavy guard. They had to find out when they would arrive and the gems were only going to be there for a day and night, stored in the bank of the town. The catch was it was a bunch of rogues (1 short range social rogue, 1 long range poison specialist, 1 trap monkey, and 1 UMD monkey) guarding it who used to have been thieves themselves. While for a mid to high level game the overuse of rogues would be detrimental, for this one it worked well, a little too well.

The PCs were captured by the rogues(not my original plan, but I had a backup in case they failed and the PCs screwed up the heist quite a bit) and were sent after the man who had hired them.