nurse on demand. at this point, if you are leaning toward weaning at some point, you can implement a "dont ask dont refuse" policy. dont ever out of nowhere offer to nurse, but dont refuse him when he wants it either
our son coslept with us and he nursed a lot at night at times too. he was between 15-17 months when he stopped waking so often at night. its better policy to comfort your baby when he is crying than leave him alone to cry, you can already see that it doesnt work, but you only know which cry is going to escalate, and which one is going to wimper off to sleep.
self soothing isnt something that babies learn, it is something that is nurtured. we did a lot of cosleeping, and after taht 15-17 months he slept in his crib in our room until yesterday :P he will be three on the 28th. and i dont regret a second; he went right to bed last night, just said he wanted to go to bed, and stayed in his crib (converted to toddler bed) and went to sleep. he did the same thing at nap time today. so waiting until he was ready was PERFECT, we have had NO struggles at bedtime, EVER in his whole 3 years of life. we have NEVER had bedtime struggles. i swear it. so do what you gotta do, it lasts for such a short time, that it will be so worth it.
but really, inside, you know what your son needs. you have the instincts. just listen to them! :) trust yourself! :)