My daughter (now 4 1/2) has never been a great sleeper either. Better since she was about 3, but still wakes occasionally, takes a specific routine to get to sleep, etc. She has also had night terrors at times. That sounds a bit like what you are describing with the waking in the middle of the night screaming, disoriented. Maybe talk to you ped or read up on that to see if that could be what is going on for the night wakings because they actually say that even though it's hard to do, not to wake them from them fully (it's actually hard to get them to wake from them- they seem awake, but aren't. Sometimes they talk to you, but they don't make sense, etc.) My daughter has had bouts of night terrors after stressful situations (we moved twice within 6 months, etc.) but they went away within say a month or so of the event). Regarding the night routine taking 2 hours, I've been there, too. Try to cut back by 15 minutes per night. Build a few visits back to the room into the "routine"- like plan on getting a cup of water for your son or tell him your leaving but will be back in a few minutes and return as planned. Your son may feel like it's not so final, but you know there's a routine with an end. Just some ideas. I've read every sleep book out there. Some of them have other good suggestions, too. Good luck!