I only hire tavern table officers, but I don't do in and out tricks. The tavern dialogue gives too high level officers, and I like serendipity playing a role in when I can meet a great surgeon--plugging in "generate this type" doesn't make for a great emergent story in my opinion.
So I don't think any action is needed on the tavern table in out trick, players can exploit the game if they choose, or not if they prefer, no point to restricting. Heck, they can just sleep in tavern day after day, it's not like crew salaries are any real restriction to that, and the player is immortal!
@Levis inded I do see where you are going, as I said I am very exciting for the system!
My disagreement was limited to the specific implementation of those 2 officer types. In general when you have two combat officers (the crazy fighter and the cautious officer) defined with combat trade offs, pluses and minuses, I don't think a third one (freebooter) should get pure combat benefits. As I explained skills negative won't matter for his role as a fighter, and given the specialization the trade off becomes a one way bonus too easily. Just some early feedback on the idea--if you decide you like that setup anyway, I'll put my concerns aside for now and happily try it in game.
Either way, I love your idea and everything you are doing for the mod!