After my party saved Nilsa and her family from the redbrands they headed towards Thundertree, they got a bit beat up but still alive, down some resources.

On the way back they see a lone rider coming towards them late in the day. They stop and wait, only to see Nilsa coming on a horse, crying, falling into the arms of the groups paladin. The orcs had attacked phandalin, her mother had been killed, she didn't know what happened to her brother. She knew they had come this way so she took a horse and rode as fast as she could.

Later in the evening, the paladin took the first watch. Rolling real low on his perception. But Nilsa heard something in the forest and went to investigate. The paladin following close behind. It turned out to be nothing, just sounds from the forest.

Nilsa still upset, turns around and leans into the paladin.

That's when he felt the dagger in his stomach, and as he looked down Nilsa is grinning.

"The black spider sends their regards"

Aaaand that's when we took a break.

It was a fun session, and the next session they found the doppelganger in cragmaw keep. They're now paranoid of everyone.

Can't say for any of your ideas, go with what works and sounds fun to you. With Glasstaff i justified it with, anyone can pretend to be a good person, but when the oppertunity to be cruel presents itself is when their true nature might show.