It's time to ask for help with these NWings.

We've always had them, F has never sttn, not even close. It was also so hard to sort through the issues because there were so many, but now at this point it seems the reflux is controlled, the intolerances outgrown, the first 8 teeth are in, and the illnesses are gone (for now), so I've been hoping it would be easier to tackle the NWings and get on track.
It used to be every night was unpredictable, and F would be waking anywhere from 3-6x a night, any time, and would sometimes settle without a feed but generally I've always fed him every 3-4hrs even at night.
Now we've settled into this pattern.
1st NWing, usually 3hrs after bedtime (between 10-11)
2nd NWing between 2-3
3rd NWing 5:30, which on occasion ends up being an EW if I can't get him back to sleep
up 6/6:30
This is more or less how it goes. At this point I figured the issues are related to habit, feeding/prop, and OT. I mean, if he were in pain they would be more random. Also, he goes right back to sleep when I feed him, so I figure if it were pain or discomfort he wouldn't go right back to sleep or he would wake again shortly after. But he just goes right back to sleep for about another 3hrs.
About a month ago I stopped feeding at the first waking because it was obviously becoming an issue. We made some progress, and after a bit he started sleeping longer first stretches, usually about 5hrs. Then we got hit with mega teething, illness, and the holidays, and I fell back into the feeding trap.
So now I am trying to tackle that first NWing again by resettling without feeding. Which is doable, I've been managing to get him back to sleep anywhere from 15-30mins the past 3 nights. But he screams bloody murder while I'm doing it. This child has a temper, and when he doesn't get what he wants he just freaks out! Now, I would have thought that after a few nights of not getting fed at that time he'd start sleeping longer. But he still wakes, and I still have to go and deal with the screaming while I resettle. Ugh!
Routine wise, it's so hard to get him enough day sleep because he just doesn't nap well. But a decent day might look something like this:
6:30 up
10 nap 45mins-1hr
2 nap 1-1.5hrs
7:15 bed
So his final A always ends up being long, and if it's been a truly bad day I try to sneak in a catnap, but it's hard because he fights it so bad.
Anyways, I can go on and on and on about our issues....

But I'll start here for now. Help, anyone?!