Thanks Vicki. I so appreciate all you ladies being here as a sounding board for me.
Well, he's been tucked up in bed asleep for the night at 4:30 today. I couldn't face another nap so we did bedtime routine and he's asleep still at 7:30. I figure he can't tell me its morning at 2am if he thinks another 9-10hr night is enough
I got to see in the light of day what's happening when he wakes screaming (yes, after two nights of plain old NW's, the screaming is back but not as intense as it had been). He's still asleep - eyes are tightly shut and he can't see, he is just sitting in bed crying really loudly and throatily. He moves away from a hand placed on him, as if he doesn't want it there

I didn't pick him up this time as I could see what was going on and he didn't want to be picked up (usually I would wait til I see him lift his arms up for me but when its pitch black, I can't tell). I just gently tried to lie him down, he sat back up a few times and continued screaming but eventually calmed down enough to find a dummy and laid himself back down. That was when he needed a gentle hand to relax back into sleep.
At least I know now how I can better handle trying to resettle when he wakes like this. Its awful seeing him like that and not being able to comfort him effectively. I so hope he sleeps tonight. His wakings haven't been as long or as loud tonight as they were previously but he is still stirring every 30-45mins and letting out a little cry. DH thought he wouldn't treat it like a night sleep since he went to bed so early but this is the best night sleep he's had in almost 3 weeks... I was not 100% sure but its the last thing I can think of that might work.