Never for such riduiculously low stakes. It's one thing when the girl you're using is also your explicit adversary (Deela, Kelinda) or the problem you're trying to resolve is the possibly un-punished murder of several family members and the possible murders of the sole remaing eyewitnesses(Lenore), another thing when--what, exactly, was Kirk's big motive here? To "pass" a test that's not designed to be passed? Again, douchebaggery, plain and simple.
EDIT: It's almost as if [SPOILER ALERT!

] you were to compare the shooting of Old Yeller to the actions of Michael Vick.
Hey all I'm saying is he's a user. It had to start somewhere. That he's channeling it for good instead of evil is commendable (I guess).

The stakes, well thats something different. Is there a good way to cheat? And what was his purpose in TWOK? "I dont like to lose."
Kirk is a douche. That the targets of his douchebaggery tends to be pompous bureaucrats (Barris, Ferris and Fox) takes the edge off, but when its a qualified Captain (Will Decker) and even his friends are calling him on it, well its harder to justify.
Wait, what was that about Ol' Yeller?????