I firmly believe that your child's personality & age has a lot to do with the methods you use to instill routine and sleeping rituals. Some babies start out brilliantly and then back track when they hit a certain age. I think it has to do with emerging personality!
Our bub is fairly placid (our first), and I keep telling her father that he's going to be in for a rude shock when our second comes along, as he/she will have a different personality...we have been spoiled with Nina!
Luckily for me, Nina has (touch wood) been very good at going off to sleep. We never vary our routine (she has a bath, then feed, then a little play. When we go to her room, her light is off, I talk to her the whole time in a low voice telling her it's time for bed, whe gets wrapped, has a cuddle and a "I love you" and is put straight into her cot wide awake (and usually smiling...in a bid to get me to pick her up...cheeky thing) Nina still has a dummy, but if she loses it during the night, she doesn't wake up for me. If she gets to an age where she does, I will consider weaning her off the dummy then. The whole ritual takes about 1 hour.
When Nina was about 2 months old we started sitting outside her door for 5 minutes at a time, and if she wasn't asleep, we'd go back in, cuddle her/settle her and leave the room again. We never left her if she became really distressed, but we could tell by her grizzles or sporadic cries that she was tired and leave her for 5 mins at a time. Within 3 days she had learned that the cot was for sleeping, and she would put herself to sleep. I don't regret starting at such a young age, and it hasn't made her anxious or clingy or stressed...so I think we did the right thing. The best thing is that now that she sleeps so well (day and night), she is an absolute joy when she is awake.
I don't know if most of it has to do with personality or parenting, but I do know that the whole thing is unfortunately a 'try and see' experience for all parents. Eventually we all have our own way of doing things and most of the time it is in response to our babies.
Good luck, I hope you sort it out soon and that hopefully it is just a 'phase' related to age and personality!!
I agree with what Julesy said bout age and personality being a deciding factor, plus what you feel comfortable in doing.
Our DD would never sleep in the day she would scream, we would cuddle her or stand and rock her cot for like 45-60mins til she fell asleep, it was a nightmare for me and her cause she's get so tired she would be beside herself.
We then did a comtrol comfort where we left the room and when she got upset went in and patted or cuddled if she was really upset but when she calmed down left again. This worked by 2 days and we learnt that our DD settles better if we aren't in her room constantly. I always thought it was wrong to leave the room until I made sure she was asleep because she would get upset if we left. But we learnt that whenever we stay in the room she gets even more upset then if we leave cause she just wants us to pick her up, which we just physically can't do constantly.
Now we put her down, she grizzles for awhile but happily goes off to sleep and we have found that she is much happier during the day and feeding better because she is not so overtired.
This worked well for us but may not work so well for another child.
I hope you find something that works for you and your son. Maybe try to have a little ritual before all sleeps so he knows. Like ours is putting her into her sleeping bag for all sleeps, cuddling while I have the CD on in the back ground and then giving her her little toy that i just give her in bed so she learns from all these cues.
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