creations, I think you had it spot on with the shorter wind down. We seem to have hit a breakthrough!! DH discovered last night that the best order is cuddle, sleep sack, then bed, where we were previously doing sleep sack, cuddle, then bed. Turns out after getting in his sleep sack thats it! He just wants to go to sleep. I just put him down for nap #2 (well, #3 really as we had to go grocery shopping and had a 30 min nap on the way there and back) and he went down so easily. For nap #1 there was no fussing at all... just in bed, lights out, asleep! I even managed to settle him to sleep in his bed when he woke after 45 mins, but then he woke 15 mins later to have a poop and that was the end of that nap!
I feel so much better that he's settling himself as he initially goes down again. And next time if I have to settle him in my arms I'll try your other trick too! Hoping that he learns to sleep through that transition soon. He definitely needs the additional sleep!