As pirates are deeply tied into my professional life IRL, I am forced to agree with you. Pirates do provide a valuable social service.
I also really like the way you bucked the trend of having pirates be dashing impulsive rogues. It's an interesting take on the old swashbuckler archetype.
I do think the two of them would get on well. Hell, he's from Denerim, it's entirely possible that she's worked with him in the past depending on what jobs she's done.