Hi Kimika
Joshua has a fluffy dog, Oscar. Oscar goes everywhere... Just a few months ago I sat him down and explained that Oscar can't go everywhere and what'll happen if Oscar gets lost???

Well, I started gradually, in the mornigs when we get to school He says bye to Oscar. He kisses and cuddles and waves bye. Then in the afternoon he knows that Oscar is waiting.
With regards to the milk, I stopped that too. J gets a bath at 7pm. Then sits on my lao and drinks bottle and 7:30 sleep time. The bottle was more comfort than anything else. Last week, J had a seroius bug and I stopped the milk feed. It's been almost a week and he seems to have forgotten about it. I spoke to his paed and he agreed that now might be a good time to stop the milk bottle. Now he only gets juice, balck rooibos(I don't take sugar and do not offer it to J either), or water.
Sometimes he'll ask for a drink at night before bed then I offer water. With all the new things happening, he also uses a cup more often than a bottle. Dh tends to offer water/tea bottle as he says J messes
Taking his comfort things away will def be traumatic. Why do you want to remove it? I find that J is alot more independent and not necessarily as clingy as he used to be. Goodluck!!!!