Convict company startup

The Plot

The PC's are imprisoned in the city dungeons for quite some time (they can be, in this scenario, homeless street urchins). They spend a few years growing older in jail, where they meet and get to know each other (you can even have one of the PC's be a Guard). The ruling council/or ruler has need of several expendable people to do various tasks for them. They can pick all the party members and have them trained and outfitted (swords, spell components, etc) to:

1. Scout out unfamiliar, dangerous land in the name of the government. Perhaps explore possible trade routes for merchants of the city, or spy on the inhabitants of a forest, etc.
2. PC's are sent as spies to a neighboring kingdom, where they are given the name of a contact to look up. Once there, they find their contact near death at an alleyway, arrows studded into his back, in hot pursuit, just as he dies he hands the PC's something (in this case, a scroll tube full of parchment). The parchment scrolls can be the report of a nasty plot to assassinate some king or queen, a list of known spies in other lands, a list of strengths and weaknesses in the army, etc.
3. PC's are assigned tasks to perform and are given little or no information (I'm taking this idea from the movie-Point of no Return).They are simply given straight forward instructions such as "Kill this noble" or "give NPC X this note then walk away". Make their simple actions turn out to be profounding. Perhaps the note they have to give to "NPC X" is an invitation to a masquerade ball sponsored by the nobility of the city their in. And the ball is the staging area for an assassination attempt on the NPC's life, etc. The PC's might even find themselves in the roll of the assassins.
4. Players can be ordered to infiltrate various underground groups that secretly oppose the government in order to reveal the identities of the members that comprise such secret orders. Perhaps the rulers need to know if a thieves or assassins guild exists without their knowing it (and the ruler thus wishes to enlist their services as spies & assassins). It could be the parties job as well to set up a meeting between the ruler they are working for and the guild master. Even more insidious would be that the ruler is secretly setting up an ambush for the guild master without the PC's knowledge (which makes it look like the PC's did it, which the ruler may desire because they've outlived their usefulness). However, with some good roleplay the Players might be able to convince the guild's second-in- command of the truth of the matter and devise a rescue attempt to free their guild master.