Oh Jen, I'm sorry about your night. I so know what you mean about feeling like torturing your baby :( DS has preferred his side for a week or so now, discovered by accident... But last night no position would do. Back, side, front (he got himself Into this position while cosleeping, worried the hell out of me, but he slept a tiny bit better, but then woke and panicked as he's not rolling yet and can't move himself off his front).
At least, as you say, you learned some from last night, but what a way to learn. Hope today isn't too bleh for you all. Here, share my cake :)
You've probably tried this, but sometimes we can get DS into his cot after falling asleep by holding him against our chests, and then, leaning into the cot, holding him close, gently lowering him a little, stopping, then lowering a bit more, stopping, and so on, until his feet touch, and then stopping, and then lowering him in totally
It totally kills my back, hovering over the mattress with a nearly 20lber, but sometimes it gets him in his cot without waking up (although we do try to get him in awake...)