Hiccups in Goal #4

So I have been trying hard to go to sleep at the same time every night with the intention of getting my full 8 hours of sleep then getting up and starting my day at a normal hour.  However, Little Man does not think I need, nor deserve 8 hours of sleep.  He has gotten into some otherworldly routine where he does not want to sleep in his own bed at night.  It's becoming a problems.

I haven't even written out my ideal bedtime routine because he's been such a little monster.  But I guess I can't blame him, and I should do my routine around him regardless.  I have a basic routine just not a set routine, which I feel I need to make this goal successful. I believe it's just my need to follow a schedule that has me set on creating this to see success, becasue without I am more whimsical and to make changes being whimsical is not going to help me.

Little Man's problems stem from not wanting to be put in his crib.  He has this inate sense when I am putting him in his crib, he wakes up, tenses his little body and starts to cry.  I try to soothe him but it's not use, he just cries, so then I let him cry.  I am trying to let him cry it out, but after an hour, I've heard enough.  So I go and get him and cuddle with him in my bed until he's asleep then I put him back in his crib.  Usually he will stay asleep then, but not always.  He has also attempted to give up napping as well. 

We have ended the midnight feedings and things were going well.  Then Little Man got sick and he started to wake up in the middle night and won't go back to sleep.  So now I have a sick child who is waking up at 1:30 and not going back to sleep until close to 4.  Then he's up again at 6 and that's when I take him into bed with me.  I would love to be up at 7 and getting ready for my day, but apparently my son has other plans for me.

I am not sure what to do, but I am open to suggestions, because I am coming to the end of my rope.  What do you do when your baby just cries and cries??  How do you get them into a good night time routine where they sleep for 8-12 hours??