Sleep Issues ....

So, I want to change the sleeping habits of my darling baby - who will be one very shortly and who I think needs a lot of help with getting to bed.
The past several nights I have basically shut off all lights, other than a simple nightlight and laid down myself. I don't really speak to him at this time, unless he lays down next to me and then I try to talk in a very soothing voice, explaining it's night-night time and giving him a bit of a massage (he likes to have his tummy or his neck rubbed!). If he gets up I don't lay him back down, nor do I tell him to lay back down. In fact I don't speak to him at all.
Generally he walks around a bit. Then he climbs on me (remember I'm laying down). Tonight he sat on my back and stayed put for a while for him. Then I think he was too tired because he kind of slid off of me, but sat and leaned back against me, and then laid down.
The first night I did this, he was awake for over an hour. Last night it was just about an hour. Tonight it was 20 minutes.
Before anyone thinks, wow, it must be working. Last night we started at 11:00 and he was asleep roughly midnight. Tonight we started at 11:40 and he was alseep at roughly midnight.
I think that the other night he probably was asleep at around midnight too.
Don't get me wrong ... I ddin't think we'd be going from midnight bedtimes to 9pm in a few days, but I would have felt much better if he wasn't staying at midnight ... even 5 minutes earlier tonight would have been nice.
Although I suppose I should have started sooner, but I lost track of time. :-(
I want to change his bedtime, but I don't want to do it by putting him in the crib and letting him cry. For one, he has yet to sleep in his crib (but once I post this I will be carrying him up and putting him in it for the first night ever). And 2, I don't think it's fair to let him have his own sleep schedule for almost 12 months and then say "well it ain't working for me, so into the crib you go and if you cry, you cry! Deal with it!" Partly because I don't think it's fair - I have taught him the habbits he has so why punish him (by making him cry) and mostly because we tried the cry-it-out method with my oldest when she was a bit over one. And it was Horrible. Horrible. It was even HORRIBLE. It was just awful and it didn't work. Basically it upset her and upset her beyond the point of being consoled and beyond the point of falling asleep. She hardly slept at all for 3 nights straight. We are talking, awake for almost 8 hours straight. It was terrible. It didn't work. We tried three nights thinking it would get betterand it didn't. It only stayed the same. And so we went back to the routine of rocking her to sleep and trying to gently move her to her crib and within a few months she learned to go to bed on her own thankfully.
However, she was never this bad. She was not up until midnight when we tried it. She was up until maybe 10, and we wanted her down closer to 9 and we wanted her down without needing to be rocked or held. But she wasn't ready - and certainly not at all to have it happen with the crying it out method.
And now here I am, 6 years later, with my son. Who is like her in so many ways, trying to figure out this whole sleep deal. But this time I'm trying it in what I hope will be a more gentler way. And I hope it really works. I have no idea if it will or not. So far being in almost complete darkness doesn't phase him - he keeps roaming around the room like I didn't just turn all the lights off.
If someone, anyone has any other ideas to try that don't involve crying at all, please, please, I beg you, shar them with me!
I am one tired mom. One beyond tired mom. Who is looking for a way to fix what I started nearly 12 months ago ....