Part 2: From seeing your posts so far I don't think that'll happen, I just thought he was interesting as an indie... So forget about it and have fun. If you ever wanna RP hit me up, my former Jedi Master is currently in limbo and transferring over to the dark side, sort of. Means he'll just explore it, maybe get himself a cool dark armor or something... Maybe they could meet, or not. I'm not even sure if he'll join the Sith, and if that's possible without him getting killed. He was the Battle Master that commanded the Alliance armed forces in the last part of the war, before the skip, so I have my doubts if they'll take kindly to him just showing up.
Part 1: Well best of luck to him then, didn't mean to say that any of the factions are bad I just wanted to point out that he simply stands out as a character. I see him being able to grow and pull of things, he's interesting and multi-sided and sometimes that can get lost. Not because of the factions necessarily but more because people fall in to these patterns of being a good-Jedi or evil-Sith.