Psyanic uses Feedback!
Is Sasha literally a rat? It gets slightly confusing because I thought Sasha was a Rattata at first given that she's picked up my Team Rocket, which made it sound like she's a Pokemon.
Anyway, I don't find that 'playing nice' would get her out of jail. Given that she's stealing (and I don't really see that as a talent; stealing is like art or plumbing - you have to build your skill) and working for a nefarious organization such as Team Rocket, I can assume Sasha is not young and would be in an actual prison or some juvenile correction facility. In either case, 'playing nice' wouldn't exactly earn her parole, but because she seems to be a bit low-ranking, I suppose she could get off early. However, there won't be too many nice kids to play with in a prison (using this interchangeably from juvenile correction facility). Her parole officer may provide a lot of interesting situations since Sasha has to report to the officer, so there's that. I can only say that it might be difficult to go to Mt. Silver when you have an officer to report to considering that Mt. Silver isn't a little hike in the woods.
Another thing is that Sasha has very little motivation to go after Red. First, you have to remember that Red practically took down the organization by himself. That alone should show how powerful of a trainer he is. Of course, it's your story and the situation could be virtually everything, but it's important to note that Red is not going to roll over. Sasha's old 'teammate's should also be in jail, so she wouldn't exactly check up on them all that frequently. Also, Sasha doesn't have a good reason to get revenge. I mean, she got picked up by an organization and it fell. So what? It's like landing a job in a company that goes bankrupt the next day. It's not your fault or anything. That sort of happened. You'll just get a new job. Sasha, to me, should move on away from crime, because look where it got her. She got in jail, not a place of unicorns and cotton candy. Your idea is fine. I like the idea of revenge fics, and I've tried playing with them myself but never get around to it, but in a story driven by revenge, there has to be a legitimate reason for revenge. Besides, if Team Rocket was on a revival, what drivers her to go after Red when she could just melt into Team Rocket once more?