Re- Plea

I know I have made this plea before, but HELP. I am at my wits end with this kid and sleeping. Everytime he's put in his bed he screams like he's been beaten and won't go to sleep. He'll easily scream for an hour each time. Every night and nap is a battle. I've read the books, articles, talked to the pediatrician and nothing works. Whenever I'm told what to try he finds a loop hole. (For example when he was younger if we let him cry he threw up all over his bed every night.) I think it's possible he's just never learned to self-soothe. He would never take a pacifier or suck his thumb and only recently seems fond of a stuffed animal or blanket. We've done "cry it out", which I HATE each time, 10+ times. It takes a week or so to work and then only lasts for a couple weeks before he's back to his old shenanigans. Each time has been more emotionally traumatizing for me and I don't really have any interest in doing it anymore since it's so awful and doesn't seem to have lasting effects. But what does that leave me? Do I quit complaining and cuddle him to sleep EVERY night? What's 10 minutes? Except then it's 20, and then 30 and then he realizes I'm going to hold him and still doesn't go to sleep.
To make matters worse, the past couple nights he's woken up and won't stop crying DURING the night. I draw the line there. Something's gotta change! So give me an idea!! I'm dying over here.
Ideas I have:
1) Take away his nap. Perhaps he's not tired enough at night? Except he seems tired, and once he's asleep still takes his 1.5 hour nap and after he's thrown his fit every night and finally falls asleep at 11-11:30 he sleeps late. So it seems he still needs the sleep he's getting.
2) Put him in a toddler bed. I've kept him in his crib because he doesn't climb out, so why transition if we don't have to? But maybe it would make him feel less trapped and more independent to climb in his bed himself? Perhaps we could start laying by him in a toddler bed?
All ideas/opinions welcome! Please!