A.P.
I breastfed my son until he was almost 2. I had intended to stop when he turned 1 but he got to grumpy and clingy. He needed me a little more. At that point I had to cut out the night feedings. It's very very hard. Not only is your son used to a snack but he's used to his favorite person in the world comforting him back to sleep. He needs to learn a new way to fall asleep. I know you need sleep and eventually it will really happen. My son, like yours wanted to eat every 3 hours or less and woke 2 times a night to snack on momma. I did what you're doing. I would tell him when the sun goes to bed every thing goes to bed, kitty goes to sleep, daddy goes to sleep, even opies (his word for breasts) goes to sleep. I would rock him for a couple minutes then put him back in his crib and sit on the floor and sing to him. I would set a limit and then I would leave his room. He would cry and bed me to come back, it broke my hear and I know it disrupted my husband but I had dealt with broken sleep half of my pregnancy and 15 months after that, he could deal with it for a week. I never let him cry more than 10 minutes without going back in to settle him down and it worked. Now he is a sleeping champ and even if I do have to go into his room now he knows momma isn't there to play for hours, just a quick snuggle and back in bed.
My son never understood how to use a sippy cup. I know it sounds crazy but he tried to treat the cup like you would the breast and that doesn't work. So I put him right onto a regular cup, he took to it fine but you might have to try a couple different types of cups to find one he likes, sippies, straws, regular. He'll take to one. Remember breastmilk is really sweet, maybe offer him a little chocolate milk or Horizon Organic Vanilla Milk, that was a big treat for my son and made him want to drink out of a cup.
Remember you're not only taking away your sons favorite nutrition you're taking away his form of security and comfort, it's hard on him. It will happen, he will wean. As with any transition some kids need a little more time. Hang in there. You did a great thing for him by breastfeeding him so long.
<3