Tish - like others have said - "do what works". If it's the pram and the sling for a little bit to get some longer sleeps into him - do whatever you have to do.
We are another family that does dinner at 4.30pm.
In terms of tired signs - we found with
DS that we had to strike like ninjas because there was a very narrow window of opportunity to get
DS to go to sleep - we worked out we had about 15 minutes max from the first yawn to get him into his sleeping bag and start settling him off to sleep, otherwise we would have to wait another couple of hours till he was soooo exhausted before we knew we would have any kind of success.
Re feeding off to sleep - I did that for every single sleep and every time he woke up during the night until he was 18 months old! I would let him go till he was practically in a coma. That meant I could be sitting there for ages with him just kind of "nibbling" away until I could detach him without him being aware of it. I used to just try and chill out to his lullaby CD and enjoy the peace and quiet. I could never leave him in the cot to just drift off.
DD yes,
DS no way.
I would also like to add that I too also have enjoyed
DS' toddlerhood far more than his babyhood. I had all the wailing banshees telling me "just wait till he's a toddler" "just you wait till he's walking" "just wait till you can't shut him up" etc etc.
None of it has come to pass. The day
DS started walking my life changed tremendously for the better. I didn't have to carry him, he was so happy to toddle along beside me. He never runs away from me at the shops. He has truly been a delight. Yes, he's had his moments - we had a small biting phase and a small headbutting phase but we came down hard on that and it was very shortlived. He's never been aggressive with other toddlers, no hitting or kicking or snatching of toys. I have very rarely raised my voice to him. I am the only mummy I know who DOESN'T own a "Toddler Taming" type of book. I just haven't needed it.
Good luck Tish! Just remember that you aren't alone, that there are other mummies out there trying desperately to get their babies to sleep too. And remember to ignore the comments from people who have never had a difficult sleeper or imply it is because you are a first-time mum "and don't really know what you're doing". They just don't get it. I can honestly say that after having
DD, I can understand why people who have never had a difficult sleeper think it's the mother's fault. I reckon it is 90% down to the temperament of the baby.