Your babe is just a day older than mine :)
I started around 7 or 8 weeks with a bedtime routine, starting around 7:30pm- bath, massage, swaddle, nurse, and books if he was still awake. Up until last week, I could lay him down awake but drowsy, turn on his little musical seahorse, and lightly rub his face and "sshhh" and he'd fall asleep, and I'd head back downstairs until I was ready for bed. We haven't been able to pull that off since daylight savings, though... He was getting tired earlier, and it took us a few days of adjusting our routine, dinner, etc... We're now working on pushing bedtime back closer to 7:30 or 8, because I (or "we," he'll be coming with me) just got a p/t job and starting two weeks from now won't be home until 6:30 most evenings. But he's been waking up 20 minutes after I put him down, then he gets overtired and cries hard- and this is not a fussy baby- and it's been taking an hour or so of DH and I trading off to get him to sleep.
I'm just trying, and really starting the past two nights or so, to be really consistent about calming him, putting him back in the cosleeper. He cries, I pick him up, calm him, put him back. It's eating up a lot of my evening, time with the husband, time to get stuff done, but I'm hoping it'll pay off.
I started today having him nap in our room with lights off/curtains pulled, swaddled like we do for nighttime, instead of downstairs in the bright kitchen in his swing. I gave in this morning and napped with him in bed with me, and he slept for two hours, but he's just now waking up after a 30 minute nap up there alone. I guess I want to get him used to going to sleep that way, although when he's napping at work with me in a few weeks, I'm sure there'll be some adjustments.
Sorry for rambling- I know that wasn't much help, since I still haven't figured this out on my own. Maybe it's the age? :)