[WARP TO...] (NOT-CANON!)
If Kestrice's brother never got captured...
"We just have some questions for you, me and my friend here. Nothing that'll take too long!"
He would probably join the republic ranks the moment he is of age (which was also what his brother did). He'd start as a trooper like everyone else but his charisma would eventually stand out to the point where spymasters of the SIS would notice.
He would eventually transfer into SIS as Skylark, as long as he is allowed to stay in touch with his brother. He would study hard and complete his training, then he would work alongside different assets and sometimes talented colleagues.
Abilities wise, he will be less survival driven (?) so pitching him against the canon him wouldnt be wise. Relies less on speed and accuracy and more on the art of conversation, preferably no bloodshed.
But he will 100% be happier. He will be in a supportive and friendly environment with his brother's support (ie cracking open a cold one together every now and then) and he'd meet great companions... and a "very good friend" 🫶
P.s it aint about him, but Pyrrhous would go up the ranks and be a great officer! He wouldnt pay much attention to his force powers, which are quite dormant without the stimulation of trauma. I can even see him having a family 🤔
Unlike the last warp post... this makes me feel warm and fuzzy. I dont really want to make kestrice sad again. This is why slavery shouldnt exist ❌