Crib Transition Help!

CLLDLL

Long time lurker, first time poster here.

So I've got a bit of a problem that I'd like to run by you AP parents to see if you have any suggestions.

With DS1 we sort of fell into bed-sharing by default.  We did that until 9 months. At that point all three of us were ready for him to "move out".  (He was a crazy restless sleeper.) He had one night of waking up every hour or two to be soothed.  Then he just magically got used to his crib and was a fabulous sleeper. 

Everything about DS2 has been different than DS1.  He wasn't interested in bed-sharing as a young infant.  He preferred swaddling and the rock-n-play and eventually blanket sleepers in the PNP.  He's always been in our room though. I BF him, and he and I both sleep better with him in the same room. We just sort of have this rhythm where I wake up as soon as he stirs, I BF him, we both go back to sleep pretty quickly. However for the last month or so he has not been waking up to BF in the MOTN. He's 8.5 months old.  He sleeps in his crib for naps pretty consistently. I think it might be time to try sleeping in the crib at night. I think he's ready. I'm just not sure I am I guess. 

My question - how would you go about transitioning him/seeing if he's ready for the transition?  I've considered putting an air mattress on the floor in the nursery and sleeping there for a few nights/weeks.  I've also considered just cold-turkey trying to lay him down in the crib to see how he does.  My biggest concerns are 1.) Him waking up in the MOTN scared and that messing up his sleep pattern 2.) My milk supply.  It's already taking a bit of a hit because of the missing MOTN feeds.  I hope it doesn't drop more once we start sleeping apart. 3.) I don't want to rush things just because society says baby should sleep in his own room. I just want to do this if it truly is what's best for both of us.

Thoughts?