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Have you read Weissbluth yet?

@grizz: If he's waking every 45, it sounds like he is relying on however you're getting him to fall asleep, to fall back asleep. I've read good things about Isis on trading down sleep associations, and as you know, we liked the no cry sleep solution which helped my LO fall asleep on his own. It was reassuring to have a plan - I decided what I was going to do, when, and that I'd stick to it for at least 4 days to see changes (it's so easy to feel like going back to'old ways' in the middle of the night!)

Online course from momsoncall.com...summarized what almost all the sleep books said (healthy sleep habits happy child, secrets of the baby whisperer, babywise). I loved it and it changed my life. So easy bc you can just view online

@grizz: I probably don't have any useful advice for you since I've only 4 weeks experience, but I can commiserate on the other people getting better naps thing because if Dh puts her down she naps fine, but for me? no chance of even getting a nap!! The only thing that works every time for me is either wearing her in the ergo or taking her in the pram!

@grizz: Is there any way you can try and replicate what the sitter does?

Does he fall asleep on his own? I had this issue with DD at this age (I was nursing to sleep) and the only thing that worked for us was to break that habit and put her down awake. We did CIO, worked like a dream.

Does he sleep in your room? It's around the 4-5 month mark that they are more aware of their surroundings. I would try having him sleep in the nursery (not in your room), and add white noise and blackout blinds. Seriously, the white noise and blackout blinds did wonders for us.

Our biggest help is using the boppy pillow for her to fall asleep in and we turn on a box fan for 'white noise' it works wonders.
She doesn't like being held to go to sleep and doesn't go to sleep in her swing or chair or anything. She likes to put herself to sleep in the boppy and then sleeps fine in her crib.

Yep, I agree with PPs who said it sounds like a sleep association/object permanence issue. Time to work on putting him down awake...the elusive drowsy but awake. I know, much easier said than done. If it's any consolation, teaching my DD to go down awake only took about a week and we didn't do CIO for that (not to say there weren't any tears, but not CIO).

Do I remember correctly that you co-bed? Are you open to moving him into his own bed (can still be in your room if you want)? Might help eliminate the nursing to sleep association.

@grizz: I won't pretend like we have sleep all figured out! Getting her to sleep both at bedtime and MOTN isn't an issue for us though and I think it really did all come together when we finally achieved drowsy but awake. The key in our case is that DH does bedtime so I'm not part of the equation and neither are the boobs! She gets a bottle if expressed milk, but I know that doesn't work for everyone. But it was the key for us. Once DH got her good at putting herself to sleep I started being able to do bedtime again

I read Weissbluth, too, and found it super helpful. Not a thrilling read by any stretch of the imagination, but it did the trick in our household. Good luck!