So far so good ladies- thanks for the support and ideas!
Night 2, bedtime routine at 7:30, fed him, in bed with a hand on his back by about 8:15. Woke up at 9:30, I stood by his crib and kept laying him down as he sat up, took about 30 minutes and he fell asleep. Woke up again at 2:30, same thing and it only took him about 20 minutes to fall asleep. Woke up at 3:45 (random), same routine, took about 15 minutes. Slept until 6:30, fed him and he was up for the day.
Night 3, bedtime routine about 7:15, fed him and in bed by 8. Woke up at 11, I let my husband attempt to follow the routine and he did good, only cried for about 20 minues. Didn't wake up again until 5:30. Fed him then and he fell back asleep until 7:45.
I am thrilled with that but I think it might be a fluke, he's a little warm today so he might have a cold which made him extra sleepy. We will see how tonight goes but overall I'm very happy with the progress.
Re: Night 2 and 3 of our sleep/soothing training