Jack might find the Luna's Call or even your own service a temporary station at some point, but I believe he may mistrust you just enough to take those so-called "wrong actions" Revan takes for the greater good as hypocrisy, due to his own misgivings. If nothing else, interactions could be fairly interesting even if they don't find each other in the same ranks or even on the same side.

Although, if it's a matter of monetary necessity and he isn't all the more aware or doesn't think anything wrong could come of it...freelancing doesn't sound like a bad idea.