As the PP said sounds like he's pushing to give up his Nap & maybe some Bedtime fears - he's at the age that nightmares & even night terrors can occur
I totally understand you on the anxiety over crying (I notice that I'm much the same with Puppy whimpering as we have a Puppy now... it's hard)
A few things to consider. Textbook ideals are just that "ideals" but from a BTDT, I've managed to raise two (I'm told by their teachers) well adjusted teens & broke many "sleep rules" along the way.
So some suggestions I have
1) try nap time in your bedroom on your bed with you, have a rest/read a book yourself & lay down the rules this is quiet time, we read our books & relax
2) If he will sleep in the stroller or the car & needs a nap use that to avoid the nap time battles.
3) Change the bedtime routine & maybe even change his room around... make it different - add/remove music, read more stories if you read them or start them if you don't etc.
For me personally I loved my children when they were toddlers, but I didn't really love spending loads of time with them & I spent every day hanging out for Nap time & bedtime for the break & I suspect that my anxiety to get them napping could have lead to some of the times we had refusal, so working out what you need from a break, rather than them needing a sleep could help too- if that makes sense.