Hi E., I didn't have the medical concerns, but I was worried my son would be upset when we stopped nursing, as he was still enthusiastic even after he turned two. We potty trained using prizes at 27 months and he felt so proud of himself. I also gave him more grown up things to do...walk at the grocery store, set the table, pick out his own books at the library, etc. So then at 28 months we used the prize system to get him to put himself to sleep at night without nursing. It was a hard two or three nights, but I would hold him on my lap and talk to him about the prize he had picked out that he could have in the morning, how we loved him and were helping him learn to go to sleep by himself, etc. These were $10 trucks that he picked out at Target, and after the potty training success, he knew he could do it, and luckily for me would even say in the morning "Mommy helped me sleep" and things along those lines. Do you know, he almost self weaned a few days after getting through the night with no nursing? He would ask once in awhile, but I would jump up and play tag or run to get a snack, or especially a drink, or something energetic that got him out of the room and situation that made him think of it. And after a week when he asked I would tell him the milk was all gone and he was OK with that. Would even look at me during the next week and instead of asking for milk would say "the milk is all gone." SO, I can give you more details if you are interested, but I was really truly pleased that it went as well as it did. When it's done gently and with love I think it goes easier...I put aside that whole week to just have lots of lap/story time, etc so he still felt close to me, but again, if he was looking for milk I would jump up and change the dynamic. Oh-one last thing, the first night of no nursing he had already picked out a truck for "when he was ready to sleep without milk", and then by total chance was exhausted and fell asleep without nursing one night. So I jumped on it and when he woke up in the middle of the night, I told him the milk was asleep and went from there. It gave him an easy first success and then the next night at bedtime we had to have Daddy come in for stories with us to give extra security about not nursing, he can do it, etc. GOOD LUCK!!! D.