Gotta love these boys huh Luey, I just wanted to let you know D still doesn't sleep well & I just follow his lead. I stopped wrapping about 6 months cause it's just getting too hot here (he often kicks the sheets off), we don't use a dummy & I still rock him most nights. He is often in bed by 8.30 & asleep by 9.30, he isn't waking up after 30 mins like he use to, it is often 3 hours until he wakes up next which doesn't sound like much but is huge for him. He will wake up another 1 or 2 times but it has settled.
Now that I have said this he will probably start waking more I know it's frustrating but I have always found the quickest way to get him to resettle is to feed him (sorry I can't remember if you are still bf or not so don't know if ff is different or not) which means I get back to sleep quicker as well. Yes I do co-sleep atm but I would still resettle this way as it means I would get back into bed quicker but this is my choice for a number of reasons.
So to answer you question in such a long winded way I have never really actively tried to get him to sleep and he isn't waking up so much, instead of every 2 hours, it's usually 3/4 hours.
HTH