Big Boy Bed??

So, lately I have been giving this a lot of thought. Just when is the right time to take the side off of Zachary's crib?
He does not try to climb out, and feels perfectly happy in his crib. I know the day I take off the side I will be regretting it, but I just feel like he is ready to be a big boy. Am I pushing it to soon? Sometimes I feel like he is that last one to do things because I am overprotective of him - perhaps. But taking the side off the crib brings on all new expenses. You cant just take off the side, you have to put up a short side so he doesn't roll off, and I will need a gate at the top of the stairs in case he comes into our room in the middle of the night in the dark. Also, does he then get sheets and a pillow, or does he continue to sleep on only a fitted sheet?
The child rolls all over the place when he sleeps - and mean ALL OVER! Each week brings less movement. In fact last night his head stayed at the top of the crib till he woke up this morning - that was a new one.
I guess what I'm asking here is for a little feedback. You truly are a lost sole with your first child!