Hiya hun
Hope you had a nice hol & that he is all better now?
Is today typical of what you have been doing most days?
I think 9am is too early for a nap after a 5am start hun - even if his night is short he's simply not ready. I wouldn't try any earlier than 9.30am or you are likely to get refusal, like today. I actually think you may be better trying to keep with the 1 nap wherever possible, & just use early bedtime to stop him getting OT. On days like today where you have 2 naps, early bedtime won't be effective, because the A time (2.5hrs after a 1hr nap) will be too short - hence why he didn't settle right away. But on a 1 nap day it will save him from the OT monster!
IIWM I would see what time he wakes tomorrow, try & keep him in bed til 6am & then shoot for a nap at 11am earliest, or 5.5hrs if he wakes after 6am. If his nap is short, do early bedtime, like we discussed previously. If he takes a 2hr nap, then aim for around 5hrs A time to BT.
What do you think?