Here we go Again, again

I thought we were all done with the sleep deprived thing.  Before Christmas we had a bad time with O for a couple of months where he wouldn't go to bed without us having to sit in his room, getting up multiple times a night etc.  What made it worse is that if he cries he throws up.  

Well, we're back to square one again.  Even bribing him with a bottle (I know it's  wrong but hey I need sleep) doesn't work.  The last several nights I have been getting up 3 or 4 x a night and sitting in his room until he falls asleep and longer because I fall asleep in the rocker.  If I had a bed in his room, I tell you I'd just bunk there.  

When we had taken him to the dr. a couple of weeks ago, the doctor said there was a lot a mucus in his throat like he had allergies.  So we've been giving him allergy medicine to see if it helped.  The mucus is what makes him gag then throw up.  We also put an air purifier in his room because lo and behold he is now sleeping in the same room his Nana used to sleep in and she developed very severe allergies while when we moved into this home.  It all seemed to help, at first.  

K doesn't want to keep giving him medicine every night because the bottle says max 2 weeks at a time.  Well, he's on it a couple of days then we stop for several then start again.  I don't know.  It can't still be his teeth can it?  We've been giving him advil before bed.  Again, you don't want to drug them up every day.  Plus he was normally a voracious bottle drinker suddenly he's cut his milk consumption down by at least half.  I'm all for it because my kids were all baba babies and it was the only hard habit we had to break so if he does it on his own.  YEAH.  Specially cause doctors and the health nurses are all dead against using bottles still.  It's such a comfort thing for my kids and normally it's not an issue.  J (who's 3) still has one a day at bedtime and she religiously asks for it because she loves it so much.  So even though I don't think it's a big deal, I am a little embarrased to admit that he still has them.  

Anyways... so any ideas on how to get him to sleep through the night?  I should mention that he doesn't make me sit in his room when he goes down for naps (crossing my fingers) cause so far I've had no problems with nap times.  

And we're talking about kid who was the easiester kid to put to bed in all time.  He goes down with his blankie and his lala (gloworm), lights out, door shut, done deal.  Why would he suddenly develop separation anxiety?

I'm at a loss. 

Zeemaid