Make sure during landing and takeoff that you have him either sucking on the bottle or nursing to prevent too much pressure buildup / his ears not popping properly/ safely. Make sure to also, do some gas relief after you land, or his tummy might bother him post flight.
I took my 9 month old to Puerto Rico, he actually slept the whole way I feel like when they get older it gets harder because sometimes they get so antsy at times. But yes I recommend taking a red eye when traveling with babies because they’re used to falling asleep around that time and will sleep the whole flight. For taking off just do the bottle you don’t want to relay on medicine all the time.
Yep we traveled to Europe with our son at 9months and home at 10 months. I preferred the nighttime flight because he basically just slept whereas I had to keep him entertained during the day. I just fed him during take off and landings if he was even awake