ha! LOVE your post...literally made me laugh outloud
As to the crate training, a young pup will need to be let out in the night to pee &/or poop. I've always paper-trained (pee pads) my yorkies for convenience of not HAVING to be home to let the dog out at regular intervals. The best setup I've found for that is to put a crate (with comfy beddingminside it) inside a playpen that is lined with pee pads. I leave the crate door open & my pups have always slept in the crate & done their business on the pads outside it.
I've never trained a pup to only go outside, but there are plenty of people on here that have, who'll be able to give you advice on how to make that type of crate training the most effective.
Congratulations on Nolita & welcome to YT
