I'm a bit confused, sorry - was that his second nap, waking at 35 and then 55 and then resettled again? How long did he go for in the end?
Oh dear I'm afraid there's such a range for getting over OT, quite dependent on what routine you're aiming for too etc. I think sometimes I've been 'lucky' and just tried the right thing for my LO and it's worked, whilst other times I too just get caught in a cycle for ages. Trouble is, they're all different and what works for one may not with another.
It's certainly possible that he doesn't need as much sleep as you're trying to get him to have, I guess a good indicator of that is to log what's actually happening together with his behaviour. But I won't pretend it's easy