Well it must be a personality thing then, because that's virtually exactly what I've done with DS most of his life... Plus he's always had a floor bed -- both a big family floor bed and a crib mattress on the floor -- not because of Montessori, I don't know much about that, but that's just what we've always had. Three years later and we are still not remotely close to kissing him goodnight & walking out the door.
Yes, we're in the same boat. DD is a long way from sleep independence, in spite of all of our efforts and routines. It's not clear to me that we're doing anything "wrong." She just won't sleep until she's good and ready....and that's been true for her entire life.