sounds like separation anxiety to me - the tipoff was the wailing, pitiful cry.
what helped us was to help ds learn object permanance. during the day, lots of peekaboo (with people or toys!), and i would tell him i was going somewhere, and then come back, etc.
at sleep times, it sounds like he's wanting reassurance that you're still there - hence that heart-wrenching cry. what i found that worked the best was to calm him down completely in his crib (pat/shh still works for us), and then walk away. when (not if) he started crying, i'd go back & repeat as often as necessary.
eventually, (usually) he'd go back to sleep for his nap.
really, we just had to ride it iout. at almost 11 months, it occasionally pops up again, but he's in much better shape now.
good luck & HTH
ps - re the bottles, you might want to check the bottle forum, but i know some moms have better luck with doing bottles right after they wake up, & in their room, where it's still a little dark & not very distracting
