K.P.
It sounds like you really do have a great bed-time routine. You could spend 2 min scratching back or patting him to comfort during the transition. I have done this with 2 of 3 boys so far. After our regular routine and prayers (love that you do that too) i would say "ok- mommy will pat on you for 2 min. and you go right to sleep"
i don't move right away after 2 min- i sit w my hand on their back for another min- then move hand and sit for 1 min- then move to door -
if they cry - i don't engage in much talk but just say "mommy is right here- you are such a big boy!" and ease on out-
i haven't ever had them just keep crying and i really have had to only go through all the extra for a good transition week or two. If he sees that he can keep you there by crying , guess what hell do??
If you know he has all he needs, and you have given a little extra encouragement - be confident that it is a good thing for him to be in his big boy bed and he will follow suit!
good luck - it sounds like you are doing a great job! hell be just fine