Missy, when I read your post about trying to fit in yoru 2 dcs, I thought "that could be me"! fwiw, we have a plan now that is showing some signs of improvement. ds's bedtime takes priority at night - bath, then I take him to bed while dh deals with dd. Feed until he stops - if he's still awake enough I read a story, and then put him down with music and endless patting - if he cries, very quick double-patting with both hands seems to help. If he cries a lot he gets picked up, cuddled, fed, whatever, and start again.
If he's falling asleep feeding I do the NCSS thing of taking him off the second he stops doing big sucks, and put him down, just so he's that little bit aware he's going to bed, plus patting, music etc, even if I think he's conked.
Did that and carried on feeding whenever for a week or so, and when he started to show signs of responding to patting - relaxing more quickly, not really fighting it, we implemented the phase we're in now, where I'm trying not to feed between 12 and 3- until 12 I feed if he wants to (though now just try cuddling and patting), try to feed at the nearest waking to 12, and then try to settle him with cuddles, singing, etc between 12 and 3. After 3 if he wakes I co-sleep with him.
It's working a bit - really, really early days, and a bad cough gave us a huge setback, but I feel better having a plan, and I think this improved calmness is transmitting to ds. What I have noticed is that the bedtime routine is definitely helping get him down for naps more easily - if I act the second he rubs his eyes, feed, bed pat sing (usually outside in pram now), he's much easier to settle.
But who knows? I have a theory, which I have repeated many times here, that much of whatr we do to change our children's behaviour as parents is stuff to keepp us busy while they grow out of it...