good luck with your challenge! I'm not sure if my experience will be any help, but just in case... ds (2 in july) has always been a terrible sleeper. the only way I've been able to get him to have a solid sleep at night (not always, but at least now it happens at all, probably more than half the time, and wake ipods aren't as long) is to give up the idea of having a couple of hours to ourselves before bed and just let him stay up til whenever he is ready, or I'm ready for bed myself! he gets at most ten hours sleep overnight, usually only about nine, but naps two hours most days and is much happier now that I don't try to force more sleep on him! I asked a gp about it because he sleeps way less than every other kid I know his age, and she said there was a finding recently that they don't need as much sleep as we assumed. so I'm telling myself he won't need constant supervision forever and just trying to suck it up...
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