I did the castle and do minutemen repeatables all the time but have no dialogue choices when talking to him, he just accepts the quest and tells me a new one. He's at Sanctuary, I know he's part of more missions and i had to do special stuff to get hancock so i'm now thinking there is still something I must do for Preston. or is he just broke. No big deal, I'm too far to go back except a restart, dont care that much about him. I have heard his perk is good.