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Okay how about this:
For whatever reason we all found each other and formed a trade caravan to try and scrape by. We quickly realized that being legit it is really hard to get by and thus decided to pursue potentially less honorable/legal means of survival. For whatever reason we've decided that just raiding and pillaging is not very classy, and it just makes everyone pissed off. So we still run our caravan, but steal when necessary or take particularly profitable jobs if we feel like it (and someone offers it). Realizing that just stealing from anyone and everyone is a good way to get killed if you aren't careful, we attempt to strike a balance between legitimate and illegitimate work, and hope to build a positive reputation with upper middle level nobles (if there are such a thing), who might pay well to have things done (as any more powerful than that they can probably just do whatever the hell they want and not worry about doing things quietly)...
Should we bring theme's into it or be like the an A-team where we are different themes but have similar goals, because there is a noble (for robin hood types).
You know, bandits, but...classy.
What I think Mckma's talking about is kind of a caravan of ne'er do wells and con men. Not above stealing, but not downright evil either. They do what it takes to survive, and if that means robbing the sorcerer kings, then so be it.
Yeah, but they do it with style. Smash and grab is too base for them, and sometimes it's more a matter of pride and "art" than just getting stuff (i.e. if life wasn't so rough, they would break into a noble's house to steal a coffee table book just to show they could)...
I'm not against a traveling caravan, but it seems a little bland. Don't get me wrong, the concept works on a number of levels, different people coming together, adventure on the open road, access to cities and towns, etc. I'd just like to see some/all of us be more than passengers, guards, what-have-you on this "stage coach". ie a hidden agenda. Like raiders traveling with the caravan with plans to attack from within when the ambush happens or some working for dragonking while others oppose them yet something happens that forces them all to work together for the survival, etc.
