I imagine after a time you do simply stop caring about the outcome of a meeting be it due to an over abundance of credits or being fed up of seeing the same old rigid lines each time. I got sick of seeing x mil or die constantly back when I was trading, there was no variation, no fun just the same old thing over and over, it's one of the main reasons I switched to a smuggler.
Playing hardmode can breathe some new life into old roles although I've found that it can quite taxing over long periods, especially if the folks you meet are irritatingly immobile in their RP.
I hope I'm right in assuming that your overall point Spazzy is to play more through your character's perspective than your own, valuing your "life" over your cargo etc? What about the lawful side of things, those who are in the position of power during these meetings, if they adopted similar ideas would they be more open to playing along, maybe even allowing you to go with only a minor fine or would they value their life and safety over yours?