A suggestion about babywearing -- mine, when ~4mos and tired, disliked being worn -- UNTIL I took him outside and walked around. That would settle him down right away. Now that he's a bit older (8mos) we don't have to go outside in order for him to like being worn. But, it may be the carrier too. He hated the moby (and we were never sling people). My favorite carriers are woven wraps and soft structured (i.e. boba). The Boba is very easy to slip on/off, and when LO falls asleep I can gently sneak him out of it .
I'd vote no for CIO also. My LO is one of those that won't settle down on his own, he just gets worked up until he passes out (not healthy). We are not on a set schedule, but he will fall asleep nursing (or in the carrier, or in my arms if I'm on the couch). If I lay in bed with him, he will toss, turn, squirm, squiggle, and eventually pass out... and then I can transfer him to his own sleeping surface. But the few times I've tried putting him in the crib, he just ended upeering out through the slats at me (or standing trying to get out). Totally not ready to fall alseep, if you kwim. I tend to let him sleep on me (in carrier) until I'm ready for bed, and then put him down when I go to sleep (we are cosleeping, but I do try to put him in the sidecar when possible).