For a while in the middle of this pregnancy I stopped making milk but he kept on comfort sucking (though complaining a bit about no milk). Now it's better for him but worse for me because I do have a bit of colostrum but he sucks so hard trying to get it!
For the last month or so we've been working aggressively on getting him to go to sleep by himself because we can't spend 45min-1.5hrs a night on that after the baby comes, and that's what it had been taking. We've resorted to a tactic I thought I'd never use: the sticker chart. It's actually working semi-well. He doesn't fuss or cry because he finds the stickers very motivating. However, it's still taking him up to an hour to actually go to sleep.