sleep issues

How can your child's sleep torture you so much that it causes you to be up all night, then think all day about it, yet never come up with a plan that lasts more than 24 hours without being questioned, doubted and redefined. Am I indecisive or just plain crazy?

We moved Noah into Dylan's bedroom last night. I had this grand plan - I would not nurse him (which I already was trying not to do between 11 and 5am) but make him go to sleep on his own - checking on him periodically. I knew it would interrupt Dylan's sleep, but I just figured I would dive in headfirst. I prepared her, and she really did pretty good. The first time he woke her up at 11:56 I thought they were both never going to stop crying. She eventually calmed down, but Noah? He was standing up awake and screaming crying from 11:56 until about 2:15. I went in every 15 minutes and reassured him. But it never stopped. Finally at 2:15 I put my hand on his back as he laid down until he fell asleep. It only took about 5 minutes. But then he was up again at 3:30. So, I did the same thing - holding my hand on his back until he fell back asleep. And he did, until about 4:50. When he woke up this time I was beat. I hadn't slept since 11:56 - questioning myself, doubting myself, trying to psyche myself up for this "sleep training." But I was done. So, I brought him into bed and nursed him back to sleep, and did that off and on for the next two hours. At least he wasn't crying anymore...

This sucks. I'm now at bedtime, night two. And I totally feel like I am doing the wrong thing. I know he needs to sleep in his own bed now - for my sanity if nothing else. And I think he should be in there with Dylan. Those things I believe. But how to make that happen is totally in question. I don't think I'm doing the right thing by leaving him in there to figure it out, so I guess I'll try to help him get back asleep tonight right away - with my hand on his back? If he can't fall asleep on his own at the beginning of the night - how am I expecting him to do so in the middle of the dark night?

Now you've seen a window to my crazy sleep world of doubt. You probably stopped reading this post last paragraph, but that's ok, it's therapeutic for me anyhow.
Why can't this be easier? Nothing in all of my three years, one month and thirteen days of parenting has caused more frustration.

I am so unsure of what I should be doing right now. So if I seem a little obsessed with pediatric sleep issues, you now know why. I need therapy.