I do think the naps area a 2-1 issue. I am a jump to it kinda person myself.
No patience here for long transitions! What about trying a nap at 11 right now and just seeing what happens? If he makes it a long one then I think you know you can keep pushing him. If it's short then sneak in a catnap. Just try to get an idea of which direction to head in, kwim?
