All kids play up in some way or other... apart from the really odd ones that sleep all through ?!?!
Jnr FD (17 months) usually sleeps quite well. However when he gets ill he usually doesnt then sleep at all well and Mrs FD usually ends up putting him in bed with her as its the only way to get him to sleep. A week later he is used to waking up and getting transferred to our bed and continues to do it when he is better.
The Mrs FD does a week of nights shifts and it falls to yours truly to get him back in to a sleeping routine in his own bed. This usually means me getting about 4 hours of broken sleep at night.
Controlled crying doesnt work with Jnr FD, he will just ball his eyes out for 2 hours until he starts chocking.
Instead I have to go in to his room, lay him back down, sing to him (I'm good you know) and after about 20 mins he will start to nod off. It can take 3 or 4 repeats of this before he ventually falls properly asleep, and then he may wake up 2 hours later and do the same thing again. However eventually he does learn he should be asleep. As it gets to the stage where he would wake up and I dont even go in the room. He may cry for 20mins or so and then drops off.
Just recovering from a week of this and just had 2 nights full sleep in a row! He will be ok now until he gets his nect illness 
I never ever give him milk in the night though. As again its just a habit thing. Try exchanging it for water to start with, as above maybe just leaving it in the room. But even that should go eventually.
Kids its all habits isnt it. I woman I work with has to get up at 4am every morning as she stupidly once let her son play downstairs one night when he wouldnt sleep. Now he thinks the day starts at 4 every morning !!
