Normal for toddler to cry going to bed?

My daughter is 20 months old and she still without fail will cry every time we put her down for a nap or for bed. She also still wakes up in the night and wants milk.

If you go in then she just wants to play and mess about and often times will just bite her cup and pretend like she’s drinking and drink nothing just to waste time.

Now we have a newborn and she’s constantly waking him up because she kicks her crib and screams and cries. I just don’t know what to do anymore. I feel like at almost 2 she should be over this stage.