For the 10 XP milestones, those are generally framed as a choice between two mutually-exclusive options.  So, for example, the 10 XP for the first milestone could be '10 XP when you stand free at last, name cleared, record clean and beholden to no one, or when you turn down your shot at freedom for the sake of helping out someone dear to you.'<br/><br/>The 1 XP trigger for Red On My Ledger seems like it would work better in the 3 XP slot, for that matter.  Perhaps as a new 1 XP option you could have '1 XP when you talk about how a current predicament reminds you of a caper from your criminal past', or something along those lines?<br/><br/>Why so Blue, Dear? looks pretty much perfect, aside from expanding out that 10 XP option.