Your routine looks good
I do think its unsafe for him to be in the cot if he is able to now jump out.... maybe time to get a big bed
As for how to respond to him at night.... I don't think you should leave him to cry it out but if he's just moaning or if its a mantra cry then I would leave him to it. Also at this age some toddlers develop fears & anxieties & it might be a good idea to get a night light. He might be freaking out at night because he is frightened of something. Too much television can do that.... if he watches tv try to limit it to daytime (maybe in the morning or just after nap)... goodness only knows what their imagination leads them to believe.
Also it could be that he is ready for less sleep overall & thats why he is harder to settle at night. My dd's sleep requirements reduces around age 2... her nap was reduced from 2hrs to 1.5 & her nights went down to 10.5hrs (from 11+hrs). So... you
could try to wake him 1.5hrs into the nap to see if he will stop the night wakings & will settle faster at night.
In any case... when he wakes at night & you see that the crying escalates, rather than leaving him to cio, I would suggest the wi/wo method. Here is the link....
https://babywhispererforums.com/index.php?topic=63896.0Just some thoughts
Layla