Hi Suzanne, Sorry I haven't read all the way through the thread so perhaps someone has mentioned this. You said on your other thread that Henry has touchy traits - you really need to take that into consideration in your handling of him
My LO1 was a touchy/sensitive baby, and paying attention to his touchy traits really paid off in STing. He really loved his routine (acted like a textbook baby when routine was right!), including the routine of his wind-down, was very sensitive to OT and OS (overstimulation), loved a long wind-down as a small baby (around your H's age), but learned how to sleep independently really really well by about 5 mos, I think. Given the sensitivity to OT, I would keep the last bit of A time super low-key, particuarly as you're pushing A times. LO1 also needed lots of physical contact, particularly if out and about, it really helped him relax. It was amazing what he could breeze through if he was in the baby carrier!
Hope some of that helps a bit.