Are these signs of under or overtired? Ready for 1 nap or no?

[QuietMouse88]

LO is 14 months. I think he’s starting the 2-1 nap transition but I’m not sure if he’s fully ready or not yet.

When on 2 naps his routine is roughly:
7am: awake
10/10.15-11am: nap for 45 mins
2.30/2.45-3.30pm: nap
8pm: bed

I have to wake him from his naps most days in order to fit the next one in. He goes down fairly well for his naps most of the time. Some days he will fight either the morning or afternoon one.

The problems are at bedtime/night time. I normally aim for 4-4.5 hour wake window before bed, depending on how tired he seems. However, it often takes him half an hour or more to go to sleep. Some nights he has a meltdown and really fights it. He’s also started waking a lot more frequently (sometimes hourly) at nighttime and it takes longer to get him back to sleep than it used to. We haven’t really had any early wakes because his nights are so disrupted and he’s woken so much that he’s shattered by morning.

When I’ve tried 1 nap and an early bedtime (when he’s pushed his morning nap so late by fighting it), he will nap for around 1.5 hours around 11.30-1pm and goes down really well at 6.30pm but he then wakes up 30 mins later really upset. On one occasion it took 2 hours to get him back to sleep as it seemed like he treated it as a nap - perhaps because bedtime was an 1.5/2 hrs earlier than normal?

Does this sound like he’s ready for 1 nap or still needs 2? I’m not sure if our issues are due to him being really overtired from such disrupted nights or undertired, causing low sleep pressure, leading to disrupted nights. Help!!

I would say just try it? When mine started the transition he would occasionally have his morning nap a bit later and it would be longer, then there wouldn't be time for the second nap or he would just not fall asleep despite wheeling him around the block in his pram to try to get him to sleep, and then on those days we would do bedtime early, like around 6pm. He eventually settled on his one nap being around 11-12.30 and bedtime has since crept from 6pm to 7pm. He dropped the nap early to be fair, he was 10 months old when he was fully on one nap having started at 8 months old.

I just let him guide us on it, I never put him on a schedule and just offer a nap whenever he would seem tired. After around 1yo we've been a bit more scheduled as otherwise bedtime is screwed, but until then I let him do what he wants. He's 16 months old now.