Thank you everyone for all your words of wisdom! In case anyone is interested on a crate training update... It still isn't going great. I've been putting him in there once or twice a day when he really needs a nap. His crying is down to 5-10 minutes which is progress
We definitely still have bad nights/early morning where we try to wait it out, but also can only take so much howling at 1am, 3am, 5am etc. This is always post bathroom break so we know that is not the issue. He doesn't seem to need or want comforting, he just wants to get out. When we try to softly comfort him with words, it has no impact, when we put our hands on the cage he just tries to really painfully gnaw on them. He is such a bad chewer so I want to get an xpen for him, but I also know that he is just going to sit in there and bark to get out even if it is right next to me.