Druuk: Caleb's very wary of the half-orc, given his past experiences. However seeing as he hasn't tried to kill anyone in front of Caleb yet, he's willing to give this half-orc the benefit of the doubt for now, even if he isn't sure if the half-orc is entirely trustworthy just yet. He at least seems martially capable at a glance, which Caleb can respect.
Lucky: He would offer the halfling the same respect he would anyone, but he wouldn't approve if he learned of his sticky fingers. However, he would probably find the halfling's general demeanor welcoming, if a bit loud for his tastes, and could be swayed if he learns or figures out that the halfling means well.
Harth-Kazann: Being aware of the stereotypes between dwarves and elves, he isn't likely to mention his elvish heritage around the dwarf unless prompted to. Otherwise, he recognizes that the dwarf, as a clergyman, believes in and fights for something greater than himself, and respects that. He would probably try to ask about the story behind the pelt at some point, in the interest of finding conversation.
Kraseawei: Given his upbringing, he wouldn't really be able to pick her out as anything more than a sailor who dresses a little strangely. So long as she doesn't try to steal anything around him, he'll try to be amicable. He's always interested in talking to a fellow bookworm, especially if she can keep up with him once he gets going about some of his favorite authors.
Colt: He would most likely find a kindred spirit in the man, given his sense of justice and distain for monsters. If he learns more about Colt, the similarity of their situations wouldn't be lost on him, which might get him to open up about things he otherwise wouldn't.
In a nutshell: He trusts some people more than others at a glance, and will try his best to be amicable and not step on toes. Otherwise, if you stay out of his way, he'll try to stay out of yours.
While aboard the ship, I imagine he'd be mostly helping the quartermaster, as he has experience with organization and logistics from his upbringing, in addition to the fifty-five pounds of steel he seemingly always wears not lending itself towards climbing around the rigging.