Hi there,
Given that your LO was an independent sleeper and you know that he can sleep independently, and having ruled out teeth/poorliness/pain, how would WI/WO?
I know with my DD, between this age and around 3years, we had a few spells, no don't leave which after a a few days started to feel like a bit of a habit and WI/WO fixed it for us.
In terms of cutting the nap/EW, can you post your LO's day - might help to figure out why your LO is waking earlier that he was. Also, could the stay with me be UT, and so is being a monkey?
HTH
Hena