Routine is key but don't bother with the should bes or shouldn't bes at this age. He's still an infant and it might take time. Some babies sleep better than others. My daughter didn't sleep all the way through the night until she was 15 months old (not saying that to scare you).
It's always a good idea to put them to bed groggy rather than fully asleep. I read that when they wake up in their crib after being put there while sleeping it's like if we, as adults, were to fall asleep in the bed and then suddenly wake up on the kitchen floor. It throws them off so make sure he knows that where he is when he falls asleep is where he is when he wakes up.
By this age, most babies need about 12-15 hours a day of sleep - 9-10 hours at night and the rest divided among daytime naps. He may wake up twice at night to eat, but he should be able to fall asleep by himself - not being held or rocked to sleep. It's a good idea not o play with him or entertain him at night. It's also important to set up daytime and nighttime routines and stick to them - same nap times & bedtime.