Hi, my ds is 5.5 and I have just started our 4th attempt at night time ddryness, all prompted by him. He hates being in pull ups and periodically gets very distressed about it.
All other times I have let him try, lifted etc and then as soon as he became dispondant about having more wet nights than dry i have gone back to the pull ups.
HOwever, this time he was really upset, and I felt that maybe I should persevere this time. Had quite a 'work up' to it, i.e. counted how many pull ups he had left and said after that many nights you can have big boy pants. Bought some cheap plastic sheets on ebay and have 3 layers of bedding/plastic sheet on for easy stripping. And then for a couple of nights before hand we practised getting his bladder to wake him (we played a game where his bladder had to shout really loud to get him awake, the louder it shouted the harder he tried to pretend he was asleep and really loved the game. When the shouting finally succeeded, we practised walking to the toilet in the dark with just a night light etc.
Basically we are 10 days in and have had 5 dry nights, the last 3 being consecutive. I had a lot of tweaking at the beginning with what time I would wake him and my phone alarm failing; now wake him twice, at 11pm and 3.30am. Don't lift him, wake him fully and get him to go to the toilet. I am resigned to having to do this for a while as he is also an extrememly heavy sleeper, but I don't mind as it is really making him happy. After a very hit and miss first week, he was despondant and wanted to go back to pull ups but i encouraged him to continue and we have made a progress chart, so that he has some visible evidence that it is getting better. (not a reward chart, because obviously it's not something he can control for now, but just as a way of seeing progress).
I am fairly sure that even if it takes a while, he will eventually get it this time. Also concur with the drinking in the daytime, if he moans when i remind him i say 'dry at night means drinking more in the day', which is greeted with i know i know but he drinks!
sorry for long post, hth.