Ah, you didn't mention his broken leg. Have you talked to the vet? If the vet says it is fully healed, it is probably stronger than the leg he didn't break.
I think you have one very smart dog. He has you wrapped around his paw. Does he still limp on that leg? And when he limps, does he get sympathy?
We had a cocker who injured one of her legs. She limped for a long time. And got sympathy. Unfortunately, she didn't remember exactly which leg had been hurt and started limping on the other -- that got her laughed at and she had too much pride to take that!
What would happen if you ignored the fact he didn't go out. Pretended to assume he didn't need to go and simply shut the door? Would he go in the house? Or would he go back to the door and ask to be let out? Rather than baby him, that is the first thing I would do. After the door was shut, I'd watch him like a hawk, to make sure he didn't potty in the house. If he really needed to go out, I think he would ask again and, this time, go out on his own. But why do that when he has a slave that will carry him into the cruel night and then give him a treat?
Ah, yes, the cuteness factor! It is a hard thing to break, but we humans have to learn not to fall for it! If you keep treating him for being cute, you will end up with a fat, bossy dog.
Try ignoring it and see what happens. Then let us know,