1. I think the Jukebox angle is just there to illustrate Kanan as a non-flat character. He's cold. His family is cold.
2. Milan's talk of no connections is awesome ... if that's mentioned and dropped. His bending over backwards to bring Tommy closer to him is ... forming ... a ... connection. He's turning into that dude from high school who swears he doesn't give a shit about his ex, but he still buys her food at lunch, talks to her on the phone every night, etc. If he doesn't want connections and being isolated makes him so powerful, keep it that way. All this successor talk is circling back to Lobos trying to pass the baton to Ghost. At least he was getting pressure and death threats as a reason to give up the game to Ghost. Milan got the whole world shook, so what's his motivation to get out? Club security business his one shot at legitimacy, Tash... Natasha!
3. Ghost's perfect life been destroyed since his murder run failed. Twice. He should've put one in Kanan's head to make sure it was done.