I think the guy in the boots is the guy that Rick and whats his name stole all his weapons out of the house boat. Remember the signs while they were on their way in?

As for Eugene he just made himself un-expendable now. He's a gold mine now and Negan knows it. With ammo starting to get short, no way would Negan let anyone hurt Eugene now. That's why he told Eugene to shut up when he was explaining how he made the bullet for Rosita. Only way he dies is if he kills himself for feeling responsible for Olivia dying.

As for Daryl good for him, glad he made his move to get out. Hope he cuts his hair too....lmao. But I think it was Jesus that left him the note. That's why he was waiting on him when Daryl pipe bombed ol Fat Boy.