Yup, that's the challenge. Lots of red herrings on this one.
1. Roy reluctantly plays along to not give away the familial recognition. That's not honest encouragement.But here's another few attempts, most of which are just as shaky.
Roy goes along with Belkar's claims that he's gay
a whole bunch of adventurers help him murder a kobold
V plays along with using the kobold's head as a litter box (IMO this is the best one I've come up with so far, but it still feels like a stretch)
And relatedly, the whole party encourages him to track down the stinky humans
2. That's Belkar hiring people to do his dirty work. They're not encouraging him, he's encouraging them.
3. Still stretching, since V is more conceding to Belkar's request rather than encouraging him to do it. Also that's Mr Scruffy taking the action in question.
4. That's not a shenanigan, that's Belkar aiding in the quest goal.