I think you're probably not getting him to bed soon enough. A classic 'mistake' is to have baby falling asleep in your arms. Transfering them to bed then is hard. Ideally, you want baby to fall asleep under the conditions under which they'll wake during the night. If the conditions are the same, they're more likely to settle off to sleep on their own. That is to say, that if baby falls asleep in your arms, they'll look for your arms when they wake to in order to go back to sleep.
HOW a baby initally falls asleep, will often dictate how/if they stay asleep or can resettle on their own.
Pat/shh in crib. I would swaddle baby as it's easier. If baby becomes very upset, pu/ but pd as soon as calm.
I had to pat/shhh my sons through some tough crying, but just stay by their side and keep up. The amount of time you have to pat/shh should decrease over a week or so as they learn to associate the pat/shh with calming.
Keep us posted.