Dropping a nap and now won’t sleep

Hi there,
My son just turned 14 months this week and has been in the process of dropping from two naps to one nap for the last month or so. He is doing this himself***
The past two weeks, I find that he is struggling to nap because he wants to be held for the entirety of the one nap. Mind you, any time he falls asleep whether for bed or nap time, I am holding him to settle him but transfer him to the crib once he’s asleep. But just recently, he wakes every time I set him down, is very difficult to resettle and ends up working himself up so much that he just stays awake.
This is a problem because he is now missing the one and only nap that he’s taking and is clearly tired and becomes quite fussy.
Does anyone have any tips or recommendations to help him sleep once put down? It’s clear that he needs this one nap but is really fighting it.

Please help

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I always try to make sure my sons tummy is full he’s 16 months so before nap time or bed time I always give him about half a cup of milk or a little less than half so it can help him be more on the full side and instead of holding him like I used to I lay him down in my bed and rub/pat/scratch his back until he falls asleep and I’ll lay with him a little bit longer when he falls asleep to make sure he’s in a deep sleep and then I’ll transfer him to his crib and for naps depending on how tired he is he’ll sleep from between 40min to an hour and a half and for bed time he usually will sleep throughout the night

unfortunately he’s also on like a hunger strike :( he’s usually a very big eater but currently isn’t each much at all and I worry he wakes cause he’s hungry but no matter what I offer, he isn’t eating. Luckily i still breastfeed but I definitely dont produce enough for him to be full all day

We put the mattress on the floor so we could lie down with our daughter when putting her to sleep (nap or bedtime)…it works so much better when she falls asleep on the mattress already instead of transferring her

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