Welcome Sherry! As for the catnap, I had a hard time getting Elsie to bed that late as well, but eventually got her used to it by doing shush/pat through a couple of entire naps - I just stayed in the room with her and started shushing and patting again every time she stirred, and then after it had been about 30 minutes I left her to wake on her own. I don't know if you're able to do that, and it might not be worth it if he's not crabby before bed. I only had to do that for a couple of naps before she got it on her own.
Don't know that I'm much help on the wind down. Here's what we do: about 10 minutes before her A time is up, I pick Elsie up and we walk around the house, and I talk quietly about going to sleep and how good a nap is going to feel. Then about 5 minutes before, we go up to her room and close the curtains, turn on her lullaby CD, and then sit in the rocker (not rocking) and I read to her in a whisper while she sits on my lap. She mostly just chews on the books. I do that until she starts to fuss, and then I put her in her sleep sack, tell her again how good her nap is going to feel, and put her in her crib. Then I hide until she starts to fuss, and then shush/pat until she falls asleep (the whole thing usually takes about 15 minutes). If I put her in her crib before the first fuss, she won't go down, and if I try to shush/pat before the 2nd fuss, she won't go down. It takes a while to figure out exactly what works for your specific LO. Good luck to you! I know it's so complicated when they refuse to cuddle or rock - before Elsie, I didn't know there was such a thing as a baby who hated those things!