Please go cold turkey. Think of it this way - if you are "gentle" and give in to a bottle of milk, you're trading for something not so gentle when your child has a mouth full of cavities and has to have dental work.
There comes a time when "gentle" is inappropriate and will result in a child being uncontrollable. Don't go down that path with your child. He needs limits and rules and expectations.
Drop the bottles. If there are no more in the house, you can't pull them out anymore. At this age, he doesn't need bottles anymore. He needs to be drinking out of a cup. It will be a hard week, but a week is nothing in the grand scheme of things.
He asks for milk when he wakes up because he likes it, but the milk is bathing his teeth with sugar, he's going back to sleep and it pools in his mouth. You aren't brushing his teeth before he goes back to sleep. No more - just water when he awakes. If he cries, too bad. He'll have to get past it. If you are 100% consistent, then he will learn the lesson.
Stop being stressed out and move him to the next developmental level. He's been treated like a one year old long enough, Mom! The next stage is wonderful too - you just have to let him cross the threshold over to it without holding onto the bottle and the milk during the night.
Dawn