The fact that the first choice is a lie doesn't seem particularly problematic on a Smuggler (especially since you don't have much reason to think that the Jedi are as messed up as they apparently are - it seems reasonable for a character to believe that the Jedi will behave in theoretical good Jedi fashion and agree to train them if they show up). Especially as it sounds like the dialogues are a little different on a Jedi. The Jedi seemed a bit weirded out by the Voss, but not contemptuous. (Or my character was busy drooling at the Ambassador and I missed something. Always possible.)

The suddenly!Racist moments baffle me, too. I'm going to go with somebody misread a memo somewhere, because they don't make much sense otherwise.