Hi newbmom ~
It's funny that you mentioned you were trying to give him cups without a lid because we tried that at dinner tonight...oh my goodness, what a mess! lol. She had water everywhere!

If you decide to go cold turkey, I think you should just do it! That's what we did over the Thanksgiving holiday with our daughter's pacifier. Even though she only took it at night, I didn't want her to be one of those kids who still needed a paci at 3 or 4 to go to bed...she cried for 45 minutes! I cried too. It was heartbreaking to say the least. It was all I could do not to run to her. However, I also realized that I was doing her a favor in the long run. And you know what? She hasn't cried since without one!
If you know that all of your son's needs are being met, then he doesn't need a bottle when waking. If you think you can "stomach the crying" then do it. I know it sounds mean, but I'm a firm believer in a good night's rest for both parties! The first few nights will be very rough because giving a bottle will be SO easy...resist the urge! He'll eventually learn that waking up does not equal food.
Please don't think I'm some horrible mom...I just really believe that this will make for healthier sleep habits. I'm sure some may disagree but I just don't see the need for bottles in the middle of the night after a certain age.
GOOD LUCK!!!