I customized your roller to choose Learned > Long Stride > Good Learner. It was pretty reliable at choosing those, but it seems on this occasion not so.
As for the questions about the crime lord, it is not an unlawful act to zap him into oblivion. Same for any neutral creature actually, apart from Guth'Alak. I'm not sure about meleeing though, since that would obviously lead to the "Are you sure?" question. I killed the crime lord to get the amulet from the sherrif so I could reach L+. I didn't get crowned till after the casino though (yes, I used casino gold, but since I also did bug-zapping and ID-hopping and xp cheats I don't consider this to be a hugely clean victory regardless). I also killed the AKW, who was obviously neutral to me.
Some other things I found to be not unlawful acts through testing:
- Attacking shopkeepers in darkness and then stealing their goods
- Ventriloquising shopkeepers to make them hostile and then stealing their wares
- Zapping the eternal guardian and bypassing him without the ring (though killing him is unlawful)
- Getting the quest to kill Guth'Alak, using a pet to kill him, and then claiming the reward from Kherab
I didn't do any of those in this game, partly out of fear that my testing might prove wrong. I was very very nervous throughout the game, worried that something could have gone wrong without me knowing. However on descending to D50 I'd almost forgotten about the whole thing, and was surprised when suddenly this "MORTAL YE HAVE DONE WELL BLAH BLAH BLAH" text came up. Was so very tempted to kill a blink dog at the end, just to see the effects... :P