With regards to the milk, firstly make sure he is having at least 100% of his recommended volume of milk throughout the day. Many babies need more milk than the amount on the tin, especially if well over the 50th centile line for weight.
That may mean more bottles per day, feeds closer together between 7am and 7pm. Add in solids meals in addition to milk, not instead of.
Once you are sure baby is getting most calories in the daytime, at bedtime do bottle, bath, book, bed. Completely separate bedtime and milk and don't worry if little of that milk is drank. Just offer it before bath and he drinks what he drinks and that's it.
Then develop an in-cot settling method. I'd use a dummy and patting in the cot until asleep. There are loads of alternates, whatever suits you.
Then go into baby as you go you bed, 11pm or whatever, with a bottle. Give a full feed, consider changing nappy if baby needs to be more awake to drink more, wind, reoffer bottle, wind again and put down to settle with a dummy.
From that point I would not feed again until morning, assuming at least 100% or recommended milk is taken know daytime, plus a dream feed. So any wakes between 11pm-7pm, settle with the in-cot settling method you use at bedtime.