What size is the quilt? If you are FMQing, yes, you can start in the middle and work your way out to the edges. You will probably want to knot and bury your thread ends; there won't be too many of them. Instead of rolling, I usually loosely accordion pleat the portion of the quilt that goes under the arm of the machine.
Is the quilt already layered? For large quilts it can be much easier to split the batting into sections to minimize bulk under the arm. Marti Michell has a book out on how to do this.