Hm, thanks for the input so far. I was definitely going about it wrong
As I understood it (drawing on past experience), you only need a role, to role play. It can be defined by the player, or assigned by the game. All that really matters is "What would
that character do in
that situation".
Consider if you were Role Playing as Gandalf in Moria and the game played out a slightly different situation that the books tell. What would Gandalf do if the hobbits were attacked? Would he hide in the shadows and try not to be seen ~leaving the hobbits to fend for themselves? What if you were Role Playing as Golem ~is that what Golem would have done?
If you are role playing your own custom character they can sometimes have some partially defined history from the game ~though they don't in TES. If you were writing a story, you would invent a main character, and over time, you would basically begin to know them, and could anticipate how they would act; and what motivates them. Its not so different with Role players. In the PNP games, people might play the same PC (or couple PC's) for years, and years. CRPG's are not advanced enough to handle regular role playing IMO, but they can come close, if they have good writers. The RPG Planescape:Torment immediately comes to mind.
I've never had occasion to play with arbitrary rules ~like 'No healing, unless in town', or no swords, or no heavy armor... etc... I never really understood that idea. I suppose that I could say that my PC doesn't know how to swim, and would never go more than chest deep into water. :shrug: ~or that... my PC is addicted to gambling, and has a hard time quitting before going broke ~and play that out in the game. That's role playing to me.
It could be that your character is just plain avarice to extreme, and will always take the path that pays money ~even if it means extortion, blackmail, or brazen opportunism, in any and all situations ~regardless of tact, or social consequences.