DS (8.5 months) is a not good but not horrendous night sleeper. Bedtime is consistently around 7:30pm (which is about the latest he can stay up without being a horrible mess). He has a nanny who feeds him dinner, bathes him, puts PJ's on him. Then I get home from work at 7:15PM and I read him books, put sleep sack on, turn the lights off and nurse him. He will get super drowsy but not fully asleep and I'll pick him up, sing to him, turn on his white noise and put him in his crib. He will then roll around holding his lovey for a few minutes and fall asleep.

Then he'll wake up sometime between 10:30 and 2 and won't go back to sleep without nursing. I've generally nursed him because he's a fast nurser. He takes both boobs and is back in bed no issues in 10 minutes. He then wakes up 3-5 hours later and we do the same routine. He then wakes up for the day at 6ish AM.

We have sleep trained for falling asleep which isn't a problem and then at 6 months we sleep trained to get rid of the first feeding since before his 4 month sleep regression he could go from 7:30 to at least 2AM. We had 2 blissful weeks of only waking up around 3-4AM but never STTN. Then he got a bad cold, a top tooth came in, he got the stomach flu, and is now on the verge of getting that second top tooth. So he is waking 2-3 times per night. Additionally he just mastered pulling to stand so when he wakes in the middle of the night he stands in his crib and screams.

From reading about sleep training, I know I really need to separate his nursing association but it's really hard when I come home from work 15 minutes before his bedtime. He's not as good of a nurser if we nurse in the light so that is frustrating. He is also really bad at taking bottles so I can't have his nanny give him a bottle before I get home.

I know we will likely have to retrain him once his tooth breaks through and he gets past this 9 month developmental stuff but I feel as if it won't stick unless I figure out how to break the nursing association. Anyone have any advice on how to improve his sleep?