hun my 3 were and still crap sleepers
i will give you last nights run down
DS1- asleep at 7pm- he always goes down easily- up at 4.45am this morning!!!
DD1- asleep at 11pm - up and 7am
boof- down at 8pm , up again at 12am and then down again at 1.30am and then up at 5am FOR THE DAY!!!!
twins did not sleep through till they were 3 years old and boof has still yet to sleep through!!!!

you have 2 choices- run with in and just go with what he wants/needs
or take some action and do some behaviour changing- ie. sleep school, control crying, or some other form
only you can make this choice
sorry no magic answers
hugs hun and will bring some toothpicks with me tommorow if that helps!!
mwah mwah mwah