27 mos. old...Should I shorten naps to improve night sleep?

[jlsmama]

Hello all,

I'm new around here, but I have recently begun to browse this wonderful forum and glean some real nuggets of wisdom. I look forward to contributing when I can, as well.

Wondering if anyone has any suggestions for my current sleep challenges. I'll aim to only include details in anticipation of relevant questions, but in short, should I shorten naps to try to improve night sleep?

My DS is 27 mos. old, has almost always been a difficult sleeper, and continues to wake 3 to 5 times per night, usually requesting a bottle of milk, occasionally requesting a brief snuggle time, and at least once to use the potty. His naps have long been solid, however; currently, every day from noon to 2 or 3pm. Might his night sleep improve if I wake him from nap after 45 mins or 1.5 hrs?

I think he wakes at night *mostly* out of habit for milk because it's like clockwork...down at 8pm, milk at 11 pm, milk at 2am, pee/sometimes milk at 3 or 4am, milk at 5 am, up at 7am. I had some previous success with limiting the milk to 1 bottle around 4 or 5am but after a season of various changes leading to my sense that he needed the comfort at night, it all went to pot and he began this frequent waking again.

For background, I'm a psychologist with a deep appreciation for attachment theory so DH and I aim to practice AP. We shared a family bed for the first six months but then made an easy transition to his room in a crib after it became apparent that he always slept better with more space on his own (even now, we try cosleeping whenever he asks but he always sleeps poorly and eventually asks to go back to his bed). He was EBF until self-weaning at 18 mos. (6 mos. after I had to go back to work full time). He tends to use milk as a soother, requesting it whenever he wants to chill out/take a break during the day. He won't drink it out of a cup. At night, he usually finishes the bottle and then either tucks it under his arm or tosses it aside. Occasionally he'll try to sleep with it in mouth.

Also, I've recently begun implementing a suggestion posted elsewhere of slowly weaning him off of milk at night by gradually watering it down in hopes that less milk will help with the frequency of night waking (also concerned about possibility of tooth decay). Do you think I should also try adjusting his naps? I've always followed his lead on the times and duration of naps and never been let down, but is it time to interfere to help reset his clock?

Thank you in advance!

[jlsmama]

Sorry, I think I may have posted this in the wrong forum. I will repost in the family bed and cosleeping forum. Please excuse my oversight...I looked for one on sleeping but didn't see it initially. :)