I like it ^^ Especially if he gets accepted into Jaxon's group, because that would cause some urgency on Crow and Penelope's side to try and get him out before the thieves are eventually captured/killed by the knights. Also, I feel like part of Jaxon's requirements for Crow when he blackmails him would be to report back to their camp every few days to let them know where the knights are searching for them, so he might run into Hartley alone then. Of course, he wouldn't openly tell Hartley that he was only working with Jaxon because he was being blackmailed, so when he and Penelope try to convince Hartley to get out of Jaxon's group later on, Hartley would probably be like "But you're with him too" and be hesitant to listen to them.
Speaking of the reports, I imagine this would be how Gavin would figure Crow out. I could see him catching him sneaking off if they're all camping together one night. Either that, or he would eventually convince Penelope to go out with him late at night to prove that Crow had turned traitor and show her that he was meeting with Jaxon (maybe they'd hide somewhere along the route that Gavin suspected Crow was taking or even follow him to his meeting place with Jaxon and eavesdrop?). Let me know what you think cx
As for the militia part, I could see the local knights training the peasants in basic fighting, since they're all on the same side, unlike the people in Brerra. I don't think it would make sense for them to jump up to knighthood or a position in the battalion from there, since the world we built operates on a feudal system where class changing would be super uncommon (Crow's case would likely be unheard of when his father makes him an ambassador, but even then he's only half peasant anyway). They could have some other kind of recognition that Hartley is after though :) Maybe they would get a title that's specifically for them, even though it wouldn't necessarily make them part of the battalion.
Also, I'll get started on my reply in like 10-20 minutes ^^