I worried about this a lot too, but we introduced the sippy cup about a month before the first birthday so our son would get the hang of the sippy. We planned on cutting out both bottles and formula cold turkey at age 1. I needlessly panicked about it, because we switched over and he didn't miss a thing.
I also panicked about cutting out the 'before bed' bottle, so what I did was put my son in his pajamas and clean diaper about 15 minutes before his actual bedtime. When I took him upstairs for night time, I turned on his music, put him in his crib, and off to sleep he went. This is the routine we used before his am and pm nap (take upstairs, turn on music, put down in crib), so I figured we'd just 'fake a nap routine' for night time. Again, no problems whatsoever.
As far as feeding, you can try to get into a 3 meals/2 snacks routine. Give your baby 6-8 ounces of milk with the meals and give your baby water with the snacks. You don't want to give much more than 24 ounces of milk daily, because like the other poster said it can lead to constipation. It can also 'falsely fill them up' where they load up on the milk but aren't hungry enough to eat the important nutritional variety in the actual 'food' from their meals.
Good luck - I found this transition to be a lot of fun, especially since it aligned more with a typical family eating schedule.