Hi Kat,
First of all, I agree with the others that it's way too early for controlled crying. Probably if there are still problems rethink your way of dealing with things when he's 5-6 months?
Second though, I do accept that you need to do something. I was in the exact same boat. My boy who is now 17 weeks slept in our bed for the first 2 months (still does after 2-3 am) & during the first 6 weeks would only fall asleep with his boob in my mouth. This meant I had to be lying next to him for naps & bedtime & it also meant I was constantly exhausted, plus agitated because every time I tried to move he cried out, woke up, & boob went in his mouth again until the next cycle! What we did is that one day I simply decided enough was enough & STOPPED doing this. I still nursed him (still do) but only sitting up in bed, & instead of my boob I offered him a dummy which he took to very very well. I have to say there was no crying involved & he simply took to the change very quickly (now of course we have a problem with dummy addiction, but that's another discussion...)
So as for the boob-to-sleep thing, I would try just stopping it, & replacing it with something else. A cuddle, a dummy, whatever works.
As for sleeping in the pram, I think that's completely normal, they all do. Maybe try to encourage more naps at home in his bed/cot/moses basket. That worked with us. My boy still loves sleeping in his pram, & has long nice naps there... but I've encouraged more & more naps in his cot, & he's simply got used to it & now seems to like his cot very much. It's a matter of being consistent & persistent, just put him where you want him to sleep again & again & he'll get the message sooner or later.
I don't know though what to suggest about the co-sleeping, because for us too that worked for a while, & still works at 2-3 am when we're just too knackered to keep going back & forth to his room. The co-sleeping has unfortunately meant no private life for the two of us, but it has also been a practical, realistic solution to easier breastfeeding & lack of sleep.
The main thing for us to remember though is that babies grow SO quickly at this stage, & so many of these problems they'll simply outgrow on their own... (hopefully!)