kitbit, my dd is only 17 months so maybe i can learn a bit from you. or i will yet eat my words. my dd used to always fall asleep on the boob. i am now at the point where i will feed her in the dark and then when she pops off on her own or when i think she's had enough, i put her in her cot.
if she is pretty awake, she becomes more awake like your ds and will stand in her cot and banter on. i let her banter on, basically ignoring her. i am at the point where i will lie on the rug quietly, a bit away from the cot and just listen. sometimes doze off even. when she begins to fuss, i go over, pick her up cuddle and or feed her and then put her back, calmer but sometimes awake or sometimes half asleep.
If she is still awake, she will chunter on some more and probably beg to be cuddled again. But after put back each time, she is quieter and after 2 or 3 times, just drifts off on her own.
At first i would put her to lie down and simply say 'lie down'. there was some tears but would put her down and sometimes cuddle her if it made her too upset. now, either dh or I stay in and say 'lie down' and she does smiling away. tonight though she was very active, in the dark, but she stayed lying down 95% of the time just chuntering away.
Like you, we did things over the summer that put any 'sleep program' back a few steps. It took just under an hour tonight. I suspect that if i had set ourselves a 'sleep plan' it would be taking less time but we had to enjoy the warm summer nights with her while we could so sleep program begone.
I am philosophical about it as it won't last forever and just lying in her room in the dark listening to her banter and sing is something to listen and enjoy as she is only a baby once and for a fleeting time in our lives. but i am not aiming (yet) for sleeping thru.