Welcome to the boards.
Just hold him, hun! He's very tiny. You don't need to be concerned about forming habits/props at this age. He'll ( and you'll) be doing well to get one nap starting in the bassinet. You can work on gently separating E and S as he gets bigger but for now there might not be much of a gap, and if there is, well, he might need a snuggle to get help him sleep. Work towards putting him down awake, but if he's mostly asleep (or even already there) don't worry. Take it one nap, one day at a time. The main thing is to avoid him getting so OT that he can't sleep. So take it easy on both of you, him crying is doing no one any good.