*Moyr looks a Syl sceptically* "It's almost like the Blues."

We've been chatty, and there's not other character which generates greater IC - OCC divergence. Moyr & Syl is a can of worms better mostly left behind but I still have some questions. I read some of Syl but not all by far, so I want some subjectivity.
Basic:
Highlight of the game?
Biggest regret?
Moment of desperation?
Dirtiest in-character thought?
And now more complex stuff.
Will Syl's mindset evolve during the long downtime? If so, in what direction? Is there a breaking point with his idea of the Empire and what currently is the Empire? What would need to happen for him to screw it and go fully renegade?
Will he have some clandestine agendas of messing with some things or just powering up?
What conditions would have to be met for his to depart the grey zone and either fully return to the Dark Side or defect to the Republic/Jedi?