Hey Spring, it sounds like he's just not sure how to wind down to go to sleep? Day times are hard (that's our prob too) because it's not as easy to do things like baths, massage etc to help relax the little ones off to sleep.

Has he always done this or is it a recent thing?

I don't have much advice because our problem is the opposite, he goes to sleep beautifully but has trouble staying asleep for extended periods and re-settling himself - it's a work in progress!

I know not everyone is a fan, but I always find when i call the Tresillian parents help line they always give great advice and suggest things I might not have thought of. Maybe give them a call? They will not encourage you to do controlled crying, so you don't have to worry about that. Can't hurt?