there is a device called a crib tent. we bought it because our DS, was very wriggly, and would get his arms or legs caught between the slats and wake up crying and in a panic. It zips closed from the outside, and should keep them contained even at two.
I work full time, so I don't do naps M-F. On Sat & Sunday, he gives strong cues and will fall asleep for 2 45 minute naps, or one lasting an 1.5 -2hrs. Bedtime hasn't been an issue as yet, because he jumps out of my arms and into his crib as soon as I start the lullaby (gues he doesn't like my singing).
I will track the responses on this question, because I suspect we have a houdini on our hands too.