I have to agree with the other comment that it depends on the baby. I am lucky that my daughter (now 10 mos) goes to sleep fairly easily in her crib for both naps and nighttime. She slept in a co-sleeper with us until four months, though. Prior to four months, she would not nap in her crib. It was almost always the swing. Now, I nurse her prior to sleepytimes and then put her in her crib. Generally she is drowsy but awake, but quite often she falls asleep while nursing.
All of this is to say that drowsy but awake is possible, but it may not be what works for everyone. If putting him down while he's asleep works, then do it that way. I really don't think he'll think the crib is evil. Also, he may not be developmentally ready for that transition. The older my child gets, the more I think you find what works for you and go with it.