I'll read the rest of the replies later, but I just want to say that Night 2 went much better than Night 1. Because it was a nice day out, he went out to play instead of watching videos after supper. He was reluctant to come in at 7:30 and start the bedtime routine, but we got through it and were in his bedroom just after 8:30 again. No nightlight because there was still light coming in the window around the blinds. (I have been asking DH to install curtains--which we have--since DS was born, but they are still not up. Maybe it can be a weekend project.)
He nursed until he was almost asleep and at 9:00 I did the PPO. He wasn't quite asleep and he wrapped himself around me while I put him into his own bed and told him it was time to go to sleep. He asked me to rub his back (which, I understand, is what they used to do at day care to get him to sleep during naps. He told me months ago that they had stopped rubbing his back at nap time but when I asked why, he said he didn't want them to do it anymore, so I didn't pursue it.) so I rubbed his back and he was asleep within 10 minutes.
He still climbed into bed with me during the night (I can't say when) and woke at 6:20 to nurse until 6:50, when we got up for the day. I skipped my shower at 6:30.