Our baby has slept in his crib in his room since he was brought home, so essentially day one in his home. I just had to believe that he would be fine in his room, and he was. In general, I think parents put their babies in their rooms b'c it makes them feel better having them closeby so we can check on them every now and then. And, whenever the weather was bad like thunderstorms, I would put our baby in his bassinet part of pack/play, and he'd sleep right beside me in our room but other than that, he's been fine in his crib in his room.
Baby monitors are awesome little devices, and ours is so loud i keep it on the mid-range level, and I can wake up in an instant when he makes a peep. Trust me, If your baby cries, you will hear it...you have k9 mommy ears, and you can and will hear everything, even the slightest sigh your baby does. My husband never hears anything at night, but I hear every little noise he makes.
You just have to decide when you want to do this and do it. I have a friend who still sleeps with her 3 yr old so I agree that you should do this sooner rather than later.
Our baby would not stay swaddled either, so I started using Halo sleepsacks (a wearable blanket). It kept his body covered, but it's more safe than a regular blanket. Babies R Us has lots of them in different styles/colors/clothweight like cotton, thermal and quilted cotton.