What's the problem with him crying if he knows you are nearby? I wouldn't lie him down at all. You can do WIWO if he responds to it, it made/makes both of my two absolutely frantic so I'm best of going in once (to check no fever/lost lovey/puke/whatever), then getting out of there and reassuring through the door - or more like, restating the rules. It's sleep time. Lie down. Not cuddles time. Lie down. Sleep now.