well def get the bottle before the new baby comes i wnet threw this my daughter was 2 n half at the time n i had my son n she would steal his bottle alot n try to be the baby i did it the wrong way i waited to long so dont do that., i def know what you mean about getting no sleep def wait till he feels better n try it they have these sippy cups with nipples on them so its a slow transtion but your getting there than after about a mo go to a reg top the kind he would have to suck to get the milk out. it might work idk thye also have these things at like walmart they come filled with juice they ahve like heads of charcters on them n you cna buy it once n just reuse those they ahve to suck it like a bottle to get the juice milk out of it thats what worked for my 3 yr old last yr.,now on the med give it to him in apple sauce or jello it works trust me i ahve 6 kids n only 2 will take meds i hope this helps you please visit my page n tell me if it works i hope your boy feels better. good luck mommy6